Product Name

  • Name

    Lilolidine

  • EINECS 691-285-6
  • CAS No. 5840-01-7
  • Article Data14
  • CAS DataBase
  • Density 1.16 g/cm3
  • Solubility
  • Melting Point 80-81°C
  • Formula C11H11 N
  • Boiling Point 318.377 °C at 760 mmHg
  • Molecular Weight 157.215
  • Flash Point 146.349 °C
  • Transport Information
  • Appearance
  • Safety 24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 5840-01-7 (Lilolidine)
  • Hazard Symbols
  • Synonyms 1,7-Trimethyleneindol;1,8-Trimethyleneindole; 5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinoline; Indole,1,7-(1,3-propanediyl)-; Lilolidene
  • PSA 4.93000
  • LogP 2.58750

Synthetic route

5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid
124730-56-9

5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

Conditions
ConditionsYield
With quinoline; copper chromite at 185℃; for 3h;93%
With quinoline; copper chromite at 185℃; for 2h;72%
With copper chromite In quinoline at 185℃; for 2h;72%
With quinoline; copper chromite at 185℃; for 4h;58%
copper(II) chromite In quinoline at 185℃; for 4h;58%
5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-one
16078-37-8

5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-one

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

Conditions
ConditionsYield
Stage #1: 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-one With diisobutylaluminium hydride In tetrahydrofuran; toluene at -20 - -10℃;
Stage #2: With hydrogenchloride In tetrahydrofuran; water; toluene at 40℃; for 0.5h; Temperature; Concentration; Reagent/catalyst;
88.9%
5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline 1,2-dicarboxylic acid
1220339-77-4

5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline 1,2-dicarboxylic acid

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

Conditions
ConditionsYield
Stage #1: 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline 1,2-dicarboxylic acid With quinoline; copper at 238℃; for 3h;
Stage #2: With hydrogenchloride In water
Stage #3: With sodium hydroxide In water
72%
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

ethylene glycol
107-21-1

ethylene glycol

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

Conditions
ConditionsYield
With Pt/Al2O3; zinc(II) oxide In neat (no solvent) at 175℃; for 24h; Sealed tube;50%
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

ethylene glycol
107-21-1

ethylene glycol

A

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

B

2-[1,2,3,4-tetrahydroquinolin-1-yl]ethan-1-ol
52704-48-0

2-[1,2,3,4-tetrahydroquinolin-1-yl]ethan-1-ol

Conditions
ConditionsYield
With palladium on activated charcoal; zinc(II) oxide In water at 150℃; for 24h; Sealed tube;A 45%
B 45%
With palladium on activated charcoal; zinc(II) oxide In water at 150℃; for 24h; Sealed tube;
quinoline
91-22-5

quinoline

ethylene glycol
107-21-1

ethylene glycol

A

1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

B

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

Conditions
ConditionsYield
With palladium 10% on activated carbon; zinc In water at 150℃; for 24h; Autoclave;A 37%
B 16%
With palladium 10% on activated carbon; zinc In water at 150℃; for 40h; Autoclave;A 33 %Spectr.
B 33 %Spectr.
With palladium 10% on activated carbon; zinc In water at 150℃; for 70h; Autoclave;A 45 %Spectr.
B 50 %Spectr.
5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid
117273-45-7

5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

Conditions
ConditionsYield
With quinoline; copper oxide-chromium oxide; hydrogen at 190℃;
[(E)-8-Allyl-3,4-dihydro-2H-quinolin-1-ylimino]-acetic acid
1026530-18-6

[(E)-8-Allyl-3,4-dihydro-2H-quinolin-1-ylimino]-acetic acid

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

Conditions
ConditionsYield
With potassium hydroxide; sulfuric acid 1.) ethanol, 120 deg C, 4 h, 2.) ethanol, reflux, 4 h; Yield given. Multistep reaction;
2-[(E)-8-Allyl-3,4-dihydro-2H-quinolin-1-ylimino]-propionic acid ethyl ester

2-[(E)-8-Allyl-3,4-dihydro-2H-quinolin-1-ylimino]-propionic acid ethyl ester

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

Conditions
ConditionsYield
With pyridine; sulfuric acid; acetic anhydride 1.) ethanol, 3.5 h; Yield given. Multistep reaction;
1-allyl-7-bromo-1H-indole
194231-71-5

1-allyl-7-bromo-1H-indole

A

1-allylindole
16886-08-1

1-allylindole

B

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene for 12h; Heating; Yield given. Yields of byproduct given;
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene for 12h; Product distribution; Heating; different N-substituted-7-bromoindoles;
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: tetrahydrofuran / 24 h / Ambient temperature
2: MgCl2 / 2-methoxy-ethanol; tetrahydrofuran / 6 h / 125 °C
3: 94 percent / aq. NaOH / ethanol / 2 h / Heating
4: 93 percent / copper chromite, quinoline / 3 h / 185 °C
View Scheme
Multi-step reaction with 2 steps
1: palladium 10% on activated carbon / 24 h / 150 °C / Autoclave
2: palladium 10% on activated carbon; zinc / water / 24 h / 150 °C / Autoclave
View Scheme
Multi-step reaction with 2 steps
1: palladium 10% on activated carbon / 24 h / 150 °C / Autoclave
2: palladium 10% on activated carbon; zinc / water / 70 h / 150 °C / Autoclave
View Scheme
5,6-dihydro-4H-pyrrolo [3,2,1-ij]quinoline-1-carboxylic acid ethyl ester
124730-53-6

5,6-dihydro-4H-pyrrolo [3,2,1-ij]quinoline-1-carboxylic acid ethyl ester

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 94 percent / aq. NaOH / ethanol / 2 h / Heating
2: 93 percent / copper chromite, quinoline / 3 h / 185 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium hydroxide; water / ethanol / 2 h / Reflux
2: copper chromite / quinoline / 2 h / 185 °C
View Scheme
3-(3,4-dihydro-2H-quinolin-1-yl)-2-oxopropionic acid ethyl ester
152712-44-2

3-(3,4-dihydro-2H-quinolin-1-yl)-2-oxopropionic acid ethyl ester

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: MgCl2 / 2-methoxy-ethanol; tetrahydrofuran / 6 h / 125 °C
2: 94 percent / aq. NaOH / ethanol / 2 h / Heating
3: 93 percent / copper chromite, quinoline / 3 h / 185 °C
View Scheme
Multi-step reaction with 3 steps
1: magnesium chloride / 2-methoxy-ethanol / 6 h / 125 °C / Reflux
2: sodium hydroxide; water / ethanol / 2 h / Reflux
3: copper chromite / quinoline / 2 h / 185 °C
View Scheme
8-allyl-1,2,3,4-tetrahydroquinoline hydrochloride
92679-18-0

8-allyl-1,2,3,4-tetrahydroquinoline hydrochloride

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 94.8 percent / CF3COOH / acetonitrile / 4 h
2: 88.6 percent / 1.8 N aq. sodium hypochlorite, 2.6 N aq. NaOH / ethanol / 1 h / 70 °C
3: 93 percent / 66percent aq. AcOH / 1 h / Ambient temperature
4: 1.) 10percent aq. H2SO4, 2.) Ac2O, pyridine / 1.) ethanol, 3.5 h
View Scheme
Multi-step reaction with 4 steps
1: 94.8 percent / CF3COOH / acetonitrile / 4 h
2: 88.6 percent / 1.8 N aq. sodium hypochlorite, 2.6 N aq. NaOH / ethanol / 1 h / 70 °C
3: 0.2percent aq. H2SO4 / ethanol / 2 h / Ambient temperature
4: 1.) aq. H2SO4, 2.) 30percent aq. KOH / 1.) ethanol, 120 deg C, 4 h, 2.) ethanol, reflux, 4 h
View Scheme
8-allyl-1-carbamoyl-1,2,3,4-tetrahydroquinoline
152771-24-9

8-allyl-1-carbamoyl-1,2,3,4-tetrahydroquinoline

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 88.6 percent / 1.8 N aq. sodium hypochlorite, 2.6 N aq. NaOH / ethanol / 1 h / 70 °C
2: 93 percent / 66percent aq. AcOH / 1 h / Ambient temperature
3: 1.) 10percent aq. H2SO4, 2.) Ac2O, pyridine / 1.) ethanol, 3.5 h
View Scheme
Multi-step reaction with 3 steps
1: 88.6 percent / 1.8 N aq. sodium hypochlorite, 2.6 N aq. NaOH / ethanol / 1 h / 70 °C
2: 0.2percent aq. H2SO4 / ethanol / 2 h / Ambient temperature
3: 1.) aq. H2SO4, 2.) 30percent aq. KOH / 1.) ethanol, 120 deg C, 4 h, 2.) ethanol, reflux, 4 h
View Scheme
8-allyl-1-amino-1,2,3,4-tetrahydroquinoline
152771-25-0

8-allyl-1-amino-1,2,3,4-tetrahydroquinoline

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 93 percent / 66percent aq. AcOH / 1 h / Ambient temperature
2: 1.) 10percent aq. H2SO4, 2.) Ac2O, pyridine / 1.) ethanol, 3.5 h
View Scheme
Multi-step reaction with 2 steps
1: 0.2percent aq. H2SO4 / ethanol / 2 h / Ambient temperature
2: 1.) aq. H2SO4, 2.) 30percent aq. KOH / 1.) ethanol, 120 deg C, 4 h, 2.) ethanol, reflux, 4 h
View Scheme
quinoline
91-22-5

quinoline

ethylene glycol
107-21-1

ethylene glycol

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

Conditions
ConditionsYield
With palladium 10% on activated carbon; zinc In water at 150℃; for 24h; Autoclave;30 %Spectr.
5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

C17H22BNO2

C17H22BNO2

Conditions
ConditionsYield
With benzylidene dichloride; C14H14N3P; N-ethyl-N,N-diisopropylamine In acetonitrile for 16h; regioselective reaction;98%
5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

2-((trifluoromethyl)thio)benzo[d]isothiazol-3(2H)-one 1,1-dioxide

2-((trifluoromethyl)thio)benzo[d]isothiazol-3(2H)-one 1,1-dioxide

1-((trifluoromethyl)thio)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

1-((trifluoromethyl)thio)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

Conditions
ConditionsYield
In 2,2,2-trifluoroethanol at 40℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube;97%
5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

C11H10(2)HN

C11H10(2)HN

Conditions
ConditionsYield
With water-d2; silver trifluoromethanesulfonate In chloroform-d1 at 90℃; for 18h; regioselective reaction;96%
5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

2-((trifluoromethyl)sulfonyl)benzo[d]thiazole

2-((trifluoromethyl)sulfonyl)benzo[d]thiazole

1-((trifluoromethyl)sulfinyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

1-((trifluoromethyl)sulfinyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

Conditions
ConditionsYield
With Diphenylphosphinic chloride In acetonitrile at 60℃; for 1h; Schlenk technique; Inert atmosphere;95%
methanol
67-56-1

methanol

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

oxalyl dichloride
79-37-8

oxalyl dichloride

sodium methylate
124-41-4

sodium methylate

(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)oxoacetic acid methyl ester
345264-02-0

(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)oxoacetic acid methyl ester

Conditions
ConditionsYield
Stage #1: 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline; oxalyl dichloride In tetrahydrofuran at 0℃; for 2.5h;
Stage #2: methanol; sodium methylate In tetrahydrofuran at -78℃;
94%
Stage #1: 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline; oxalyl dichloride In tetrahydrofuran; dichloromethane at 0℃; for 0.5h;
Stage #2: methanol; sodium methylate In tetrahydrofuran; dichloromethane at -78 - 20℃; for 2h;
87%
5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione
4290-72-6

5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione

Conditions
ConditionsYield
With oxygen; Rose Bengal lactone In water; N,N-dimethyl-formamide for 48h; Inert atmosphere; Irradiation;93%
5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

2-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol

2-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol

Conditions
ConditionsYield
With copper diacetate; 4,4'-di-tert-butyl-2,2'-bipyridine at 90℃; for 24h; Schlenk technique; regioselective reaction;92%
5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

2-vinylbenzaldehyde
28272-96-0

2-vinylbenzaldehyde

8-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-13-methyl-5,6-dihydro-4H-benzo[b]pyrido[3,2,1-jk]carbazole

8-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-13-methyl-5,6-dihydro-4H-benzo[b]pyrido[3,2,1-jk]carbazole

Conditions
ConditionsYield
With dipotassium peroxodisulfate; tetrakis(acetonitrile)palladium bistriflate In acetonitrile at 60℃; for 18h; Inert atmosphere; Schlenk technique; Sealed tube; regioselective reaction;91%
2,6-Dichloropyrimidine
3934-20-1

2,6-Dichloropyrimidine

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

1-(2-chloropyrimidin-4-yl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

1-(2-chloropyrimidin-4-yl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

Conditions
ConditionsYield
Stage #1: 2,6-Dichloropyrimidine With aluminum (III) chloride In 1,2-dimethoxyethane at 20℃; for 0.333333h;
Stage #2: 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline In 1,2-dimethoxyethane at 80℃; for 6h;
90.1%
With iron(III) chloride In 1,2-dichloro-ethane at 60℃;
Stage #1: 2,6-Dichloropyrimidine With aluminum (III) chloride In 1,2-dimethoxyethane at 20℃; for 0.333333h;
Stage #2: 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline In 1,2-dimethoxyethane at 80℃; for 6h;
Stage #1: 2,6-Dichloropyrimidine With aluminum (III) chloride In 1,2-dimethoxyethane at 20℃; for 0.333333h;
Stage #2: 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline In 1,2-dimethoxyethane at 80℃; for 6h;
5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

Thiram
137-26-8

Thiram

5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl N,N-dimethylaminodithioformate

5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl N,N-dimethylaminodithioformate

Conditions
ConditionsYield
With dipotassium peroxodisulfate; potassium iodide at 60℃; for 12h;89%
With dipotassium peroxodisulfate; potassium iodide In water; N,N-dimethyl-formamide at 60℃; for 12h; Green chemistry;89%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

1,3-dioxoisoindolin-2-yl (3r,5r,7r)-adamantane-1- carboxylate
118334-83-1

1,3-dioxoisoindolin-2-yl (3r,5r,7r)-adamantane-1- carboxylate

1-(2-(-adamantan-1-yl)-1-(4-methoxyphenyl)ethyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

1-(2-(-adamantan-1-yl)-1-(4-methoxyphenyl)ethyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

Conditions
ConditionsYield
With indium(III) triflate; tris[2-phenylpyridinato-C2,N]iridium(III) at 30℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation;88%
5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

1,1,1-trifluoro-2-phenylbut-3-yn-2-yl 2,3,4,5,6-pentafluorobenzoate

1,1,1-trifluoro-2-phenylbut-3-yn-2-yl 2,3,4,5,6-pentafluorobenzoate

C21H16F3N

C21H16F3N

Conditions
ConditionsYield
With 4-methyl-morpholine; copper(I) triflate benzene complex; 2,6-bis[(4S,5R)-4,5-diphenyl-4,5-dihydro-1,3-oxazol-2-yl]pyridine In methanol at 0℃; for 24h; Schlenk technique; Inert atmosphere; enantioselective reaction;86%
5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

sodium methylate
124-41-4

sodium methylate

(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)oxoacetic acid methyl ester
345264-02-0

(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)oxoacetic acid methyl ester

Conditions
ConditionsYield
Stage #1: 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline; oxalyl dichloride In diethyl ether at 0℃; for 0.5 - 0.75h;
Stage #2: sodium methylate In methanol; diethyl ether at -78 - 20℃;
85%
5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

oxalyl dichloride
79-37-8

oxalyl dichloride

sodium methylate
124-41-4

sodium methylate

(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)oxoacetic acid methyl ester
345264-02-0

(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)oxoacetic acid methyl ester

Conditions
ConditionsYield
Stage #1: 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline; oxalyl dichloride In diethyl ether at 0℃;
Stage #2: sodium methylate In methanol at -78 - 20℃;
85%
Stage #1: 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline; oxalyl dichloride In diethyl ether at 0℃; for 0.666667h;
Stage #2: sodium methylate In methanol; diethyl ether at -78 - 24℃; for 2h;
84%
5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

sodium trifluoroethylsulfinate

sodium trifluoroethylsulfinate

1-((2,2,2-trifluoroethyl)thio)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]-quinoline

1-((2,2,2-trifluoroethyl)thio)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]-quinoline

Conditions
ConditionsYield
With chloro-trimethyl-silane; phosphonic acid diethyl ester In acetonitrile at 85℃; for 3h; Sealed tube;85%
5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

ethyl 2-diazo-3-oxobutanoate
2009-97-4

ethyl 2-diazo-3-oxobutanoate

ethyl 2,2-bis(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-3-oxobutanoate

ethyl 2,2-bis(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-3-oxobutanoate

Conditions
ConditionsYield
With air In 2,2,2-trifluoroethanol; water at 120℃; for 12h; Sealed tube;85%
5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

diethyl (bromodifluoromethyl)phosphonate
65094-22-6

diethyl (bromodifluoromethyl)phosphonate

1-((difluoromethyl)thio)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

1-((difluoromethyl)thio)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

Conditions
ConditionsYield
Stage #1: 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline With water; iodine; thiourea; potassium iodide In 1,4-dioxane at 50℃;
Stage #2: With sodium hydroxide In 1,4-dioxane at 50℃; for 1h;
Stage #3: diethyl (bromodifluoromethyl)phosphonate In 1,4-dioxane at 20℃; for 4h;
80%
1,2,4-Triazole
288-88-0

1,2,4-Triazole

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

C13H12N4

C13H12N4

Conditions
ConditionsYield
With 5-ethyl-1,3,7,8-tetramethylalloxazinium triflate; iodine; oxygen In acetonitrile at 50℃; under 760.051 Torr; for 36h; Green chemistry;79%
5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

C22H20N2

C22H20N2

Conditions
ConditionsYield
With oxygen; palladium diacetate; acetic acid In dimethyl sulfoxide at 40℃; under 760.051 Torr; for 24h; regioselective reaction;76%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

acetonitrile
75-05-8

acetonitrile

4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(4-methoxyphenyl)butanenitrile

4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(4-methoxyphenyl)butanenitrile

Conditions
ConditionsYield
With indium(III) triflate; silver carbonate at 120℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;75%
NH-pyrazole
288-13-1

NH-pyrazole

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

C14H13N3

C14H13N3

Conditions
ConditionsYield
With 5-ethyl-1,3,7,8-tetramethylalloxazinium triflate; iodine; oxygen In acetonitrile at 50℃; under 760.051 Torr; for 36h; Green chemistry;75%
5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

difluoromethylsulfinyl chloride

difluoromethylsulfinyl chloride

1-((difluoromethyl)thio)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

1-((difluoromethyl)thio)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

Conditions
ConditionsYield
In acetonitrile at 90℃; for 6h; Inert atmosphere;73%
5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

2,2,2-trifluoroethanol
75-89-8

2,2,2-trifluoroethanol

1-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-2,2,2-trifluoroethan-1-ol

1-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-2,2,2-trifluoroethan-1-ol

Conditions
ConditionsYield
With copper diacetate; 4,4'-di-tert-butyl-2,2'-bipyridine at 90℃; for 24h; Schlenk technique; regioselective reaction;73%
5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

C19H17NO4

C19H17NO4

1-((2R,4R,4aR,10aS)-4-(nitromethyl)-2-phenyl-3,4,4a,10a-tetrahydro-2H,5H-pyrano[2,3-b]chromen-2-yl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

1-((2R,4R,4aR,10aS)-4-(nitromethyl)-2-phenyl-3,4,4a,10a-tetrahydro-2H,5H-pyrano[2,3-b]chromen-2-yl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane at 0℃; Inert atmosphere; Molecular sieve; chemoselective reaction;72%
5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

2,2'-diiodobiphenyl
2236-52-4

2,2'-diiodobiphenyl

C23H17N

C23H17N

Conditions
ConditionsYield
With palladium(II) trimethylacetate; silver carbonate In dimethyl sulfoxide; N,N-dimethyl-formamide at 80℃; for 19h;72%
5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

4-chloro-6,7-bis(2-methoxyethoxy)quinazoline
183322-18-1

4-chloro-6,7-bis(2-methoxyethoxy)quinazoline

1-(6,7-bis(2-methoxyethoxy)quinazolin-4-yl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

1-(6,7-bis(2-methoxyethoxy)quinazolin-4-yl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

Conditions
ConditionsYield
With 1,1,1,3',3',3'-hexafluoro-propanol; bis(trifluoromethanesulfonyl)amide at 100℃; for 6h; Sealed tube;72%
5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine
24415-66-5

7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

1-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolinone

1-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolinone

Conditions
ConditionsYield
With 1,1,1,3',3',3'-hexafluoro-propanol; bis(trifluoromethanesulfonyl)amide at 100℃; for 6h; Sealed tube;72%
With 1,1,1,3',3',3'-hexafluoro-propanol; bis(trifluoromethanesulfonyl)amide at 100℃; for 6h; Microwave irradiation; Sealed tube;72%

Lilolidine Chemical Properties

Molecule structure of Lilolidine (CAS NO.5840-01-7):

Molecular Weight: 157.2117 g/mol
Molecular Formula: C11H11N
Density: 1.166 g/cm3
Melting Point: 80-81°C
Boiling Point: 318.377 °C at 760 mmHg 
Flash Point: 146.349 °C
Index of Refraction: 1.656
Molar Refractivity: 49.546 cm3
Molar Volume: 134.785 cm3
Polarizability: 19.641×10-24 cm3
Surface Tension: 44.838 dyne/cm  
Enthalpy of Vaporization: 53.758 kJ/mol
Vapour Pressure: 0.001 mmHg at 25 °C 
InChI: InChI=1/C11H11N/c1-3-9-5-2-7-12-8-6-10(4-1)11(9)12/h1,3-4,6,8H,2,5,7H2 Copy
InChIKey: QCCKSFHMARIKSK-UHFFFAOYAA 
Product Categories of Lilolidine (CAS NO.5840-01-7): Pale White Powder

Lilolidine Specification

 Lilolidine (CAS NO.5840-01-7) is also named as 2,3-dihydro-1H-pyrrolo[3,2,1-ij]quinoline ; 5,6-dihydro-4h-pyrrolo[3,2,1-ij]quinoline ; 1,7-Trimethyleneindole .

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