Rutaecarpine supplier | CasNO.84-26-4

Name
Rutaecarpine
EINECS 635-907-6
CAS No. 84-26-4
Article Data82
CAS DataBase
Density 1.456 g/cm³
Solubility DMSO: 18 mg/mL
Melting Point 259.5 - 260oC
Formula C₁₈H₁₃N₃O
Boiling Point 550.072 °C at 760 mmHg
Molecular Weight 287.321
Flash Point 286.473 °C
Transport Information UN 2811 6.1/PG 3
Appearance white solid
Safety 45
Risk Codes 25
Molecular Structure
Hazard Symbols T
Synonyms Rutaecarpine;Rutecarpine(6CI,7CI,8CI);NSC 258317;Rhetine;
PSA 50.68000
LogP 3.10090

Synthetic route

: 95274-40-1
3b-trifluoromethyl-13b,14-dihydrorutaecarpine

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
With hydroxide In ethanol; water for 0.75h;	100%
With potassium hydroxide In ethanol for 0.25h; Heating;	96%
With base Yield given;

: 80783-78-4
6-phenyl-hydrazono-6,7,8,9-tetrahydro-11-oxo-11H-pyrido[2,1-b]-quinazoline-hydrochloride

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
With PPA at 180℃; for 0.5h;	98%
With PPA at 160 - 180℃; for 0.333333h;	98%

: 459157-64-3
2-cyano-3-[2-(indol-3-yl)ethyl]-4(3H)-quinazolin-4-one

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
With hydrogenchloride at 120 - 130℃; for 3.5h;	95%

: 80776-66-5, 81589-34-6, 95610-41-6
(E)-6-(2-phenylhydrazono)-8,9-dihydro-6H-pyrido-[2,1-b]quinazolin-11(7H)-one

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
With PPA at 180℃; Fischer indole synthesis;	95%
With polyphosphoric acid at 160 - 180℃; for 1h;	83%
With H-mordenite; acetic acid for 5h; Heating;	82%
With PPA at 180℃; for 1h;	270 mg

: 80776-66-5, 81589-34-6, 95610-41-6
6-phenylhydrazono-6,7,8,9-tetrahydro-11H-pyrido<2,1-b>quinazolin-11-one

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
With PPA at 160 - 180℃; for 0.333333h;	94%
With PPA at 180℃; for 0.5h;	92%
With acetic acid; zinc(II) chloride for 5h; Fischer Indole Synthesis; Reflux; Inert atmosphere;	65.6%

: 88783-83-9
N-(2-nitrobenzoyl)-1-oxo-1,2,3,4-tetrahydro-β-carboline

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
Stage #1: N-(2-nitrobenzoyl)-1-oxo-1,2,3,4-tetrahydro-β-carboline With hydrogenchloride; tin In methanol Stage #2: With sodium hydroxide; triethylamine In dichloromethane Further stages.;	94%
Stage #1: N-(2-nitrobenzoyl)-1-oxo-1,2,3,4-tetrahydro-β-carboline With hydrogenchloride; tin In methanol; water at 20℃; for 12h; Stage #2: With sodium hydroxide; triethylamine In dichloromethane; chloroform; water for 3h;	69.9 mg

: 4894-26-2
3,4-dihydro-β-carboline

: 118-48-9
isatoic anhydride

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 95℃; for 20h; Inert atmosphere;	93%

: 17952-82-8
1,2,3,4-tetrahydronorharman-1-one

: 134-20-3
2-carbomethoxyaniline

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
Stage #1: 1,2,3,4-tetrahydronorharman-1-one With hydrogenchloride In chloroform Stage #2: With trichlorophosphate at 40℃; for 2h; Stage #3: 2-carbomethoxyaniline In tetrahydrofuran at 20℃; for 12h;	92%

: 2-(2-azidobenzoyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
With hydrogenchloride In methanol at 52℃; for 0.0333333h; Microwave irradiation;	90%
With tributylphosphine In benzene at 60℃; for 2h;	71%

: 754123-75-6
1-(methylthio)-4,9-dihydro-3H-pyrido[3,4-b]indole

: 118-92-3
anthranilic acid

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
In acetic acid for 24h; Heating;	85%
With acetic acid for 12h; Reflux;	80%
With acetic acid for 24h; Reflux; Inert atmosphere;	44%

: 4894-26-2
3,4-dihydro-β-carboline

: 118-92-3
anthranilic acid

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25 - 80℃; Schlenk technique;	85%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 80℃;

: 17952-82-8
1,2,3,4-tetrahydronorharman-1-one

: 118-92-3
anthranilic acid

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
With thionyl chloride In benzene	82%
With triethyloxonium fluoroborate

: C19H17N3O2

A: C18H13N3O

B: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
With hydrogenchloride In butan-1-ol at 120℃; for 168h;	A 5% B 81%

: (2-aminophenyl)(1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indol-2-yl)methanone

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
With tert-butylammonium hexafluorophosphate(V) In acetonitrile at 70℃; for 4h; Electrochemical reaction; Green chemistry;	80%
With (5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato)iron(III) chloride; [bis(acetoxy)iodo]benzene In toluene at 110℃; for 3h; Inert atmosphere; Schlenk technique; Molecular sieve;	79%
With potassium tert-butylate; oxygen; copper(I) bromide In dimethyl sulfoxide at 100℃; Schlenk technique; regioselective reaction;	60%

: 118-48-9
isatoic anhydride

: 16502-01-5
tetrahydrobetacarboline

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In ethanol at 75℃; Electrochemical reaction;	80%
Multi-step reaction with 2 steps 1: toluene / 100 °C 2: copper(I) bromide; potassium tert-butylate; oxygen / dimethyl sulfoxide / 100 °C / Schlenk technique View Scheme

: 16502-01-5
tetrahydrobetacarboline

: 271-58-9
anthranil

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
In toluene at 130℃; for 1h;	78%
In toluene at 130℃;

: 16502-01-5
tetrahydrobetacarboline

: 91-56-5
indole-2,3-dione

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
With tert.-butylhydroperoxide In water at 100℃; for 12h; Green chemistry;	77%

: 98260-32-3
2-chloro-3-<2-(indol-3-yl)ethyl>-4(3H)-quinazolinone

A: 4119-10-2
3-(2-(1H-indol-3-yl)ethyl)-quinazolin-2,4(1H,3H)-dione

B: 84-26-4
rutaecarpine

C: 142834-66-0
3-(2-aminophenyl)-1,2,3,9-tetrahydropyrrolo<2,1-b>quinazolin-9-one

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water for 17h; Ambient temperature;	A 20% B 9% C 70%
With hydrogenchloride In methanol; water for 17h; Mechanism; Ambient temperature;	A 20% B 9% C 70%

...Expand

: 38750-15-1
Rutaecarpane

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
With potassium permanganate In acetone for 3h; Reflux;	68%
With potassium permanganate In acetone for 2h; Heating;	61%
Stage #1: Rutaecarpane With tert.-butylhydroperoxide; potassium iodide In decane; ethanol at 20℃; for 36h; Inert atmosphere; Stage #2: With piperidine In decane; ethanol at 50℃; for 1h; Inert atmosphere;	58%

: 33284-02-5
2-amino-N-[2-(1H-indol-3-yl)ethyl]benzamide

: 3724-43-4, 149409-22-3
Vilsmeier reagent

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
at 150℃; for 0.833333h; Ionic liquid; Inert atmosphere; Microwave irradiation;	68%

: 1316852-05-7
N14-tertiobutoxycarbonyl-7,8,13,13b-tetrahydroindolo-[2',3':3,4]pyrido[2,1-b]quinazolin-5-one

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
With potassium tert-butylate; oxygen In N,N-dimethyl-formamide at 20℃; for 7h;	67%

: 4894-26-2
3,4-dihydro-β-carboline

: 201230-82-2
carbon monoxide

: 615-43-0
2-iodophenylamine

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
With manganese(IV) oxide; potassium phosphate; bis(tri-t-butylphosphine)palladium(0) In toluene at 120℃; under 760.051 Torr; for 12h; Inert atmosphere; Schlenk technique;	67%

...Expand

: 807354-70-7
3-[2-(N-acetyl-2-bromoindol-3-yl)ethyl]-4(3H)-quinazolinone

A: 84-26-4
rutaecarpine

B: 60941-86-8
3-<2-(3-indolyl)ethyl>-4(3H)-quinazolinone

C: 807354-69-4
3-[2-(2-bromoindol-3-yl)ethyl]-4(3H)-quinazolinone

Conditions

Conditions	Yield
With palladium diacetate; tetrabutyl-ammonium chloride; potassium acetate In N,N-dimethyl-formamide for 0.5h; Product distribution; Further Variations:; Reagents; Heating;	A 16% B 63% C 12%

...Expand

: 5344-90-1
2-Aminobenzyl alcohol

: 16502-01-5
tetrahydrobetacarboline

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
With oxygen; toluene-4-sulfonic acid; copper(I) bromide In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 12h;	63%

: C18H15N3O2

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	61%

: 881914-20-1
2-(4,9-dihydro-3H-β-carbolin-1-ylamino)-benzoic acid methyl ester

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 12h;	58%

: 34897-85-3
o-azidobenzoyl chloride

: 3,4-dihydro-β-carboline hydrochloride

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 48h; Inert atmosphere;	58%

: 807354-69-4
3-[2-(2-bromoindol-3-yl)ethyl]-4(3H)-quinazolinone

A: 84-26-4
rutaecarpine

B: 60941-86-8
3-<2-(3-indolyl)ethyl>-4(3H)-quinazolinone

Conditions

Conditions	Yield
With air; tri-n-butyl-tin hydride In hexane; toluene at 20℃;	A 8% B 57%

: 807354-69-4
3-[2-(2-bromoindol-3-yl)ethyl]-4(3H)-quinazolinone

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
With hexamethyldistannane In various solvent(s) at 150℃; for 6h; Irradiation;	55%

: 95274-56-9
14-trifluoroacetyl-8,13,13b,14-dihydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one

: 84-26-4
rutaecarpine

Conditions

Conditions	Yield
With dihydrogen peroxide; potassium hydroxide In ethanol; water at 20 - 60℃; for 10.5h; Inert atmosphere;	53%

: 84-26-4
rutaecarpine

A: 38750-15-1
Rutaecarpane

B: 38750-16-2
Rutaecarpene

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 8h;	A 3% B 97%
Stage #1: rutaecarpine With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 6h; Stage #2: With hydrogenchloride; water In tetrahydrofuran

: 84-26-4
rutaecarpine

: 107-13-1
acrylonitrile

: 3-(5-oxo-7,8-dihydro-5H-indolo[2',3':3,4]pyrido[2,1-b]quinazolin-13-yl)-propionitrile

Conditions

Conditions	Yield
With Triton B In N,N-dimethyl-formamide at 20℃; for 3h;	95%

: 84-26-4
rutaecarpine

: 105-36-2
ethyl bromoacetate

: ethyl (5-oxo-7,8-dihydro-5H-indolo[2',3':3,4]pyrido[2,1-b]quinazolin-13-yl)-acetate

Conditions

Conditions	Yield
Stage #1: rutaecarpine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h; Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide at 20℃; for 4h;	94%

: AuCl4*4H2O

: 84-26-4
rutaecarpine

: AuCl4*C18H13N3O*H(1+)

Conditions

Conditions	Yield
In methanol; chloroform at 55℃; for 3h; Temperature;	87.1%

: 84-26-4
rutaecarpine

: 8,13-tetrahydroindolo[2',3':3,4]pyrido[2,1-b]quinazoline-5(7H)-thione

Conditions

Conditions	Yield
With Lawessons reagent In toluene for 4h; Heating;	85%
With pyridin-1-ium-1-yl[pyridin-1-ium-1-yl(sulfido)phosphinothioyl]sulfanyl-sulfido-thioxo-phosphane In sulfolane at 100 - 135℃; for 0.333333h;	70%
With Lawessons reagent In toluene at 110℃; for 6h;	54.5%

: 30729-25-0, 25794-47-2, 15274-33-6, 22840-91-1, 75992-73-3, 14568-13-9
dichlorobis(dimethylsulfoxide)platinum(II)

: 84-26-4
rutaecarpine

: C20H19Cl2N3O2PtS

Conditions

Conditions	Yield
In methanol; chloroform at 65℃; for 6h; Temperature;	81.4%

: 84-26-4
rutaecarpine

: 55786-24-8
7,8-Dehydrorutecarpine

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane for 0.5h; Reflux;	80%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane for 0.5h; Heating;	75%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane at 50 - 80℃; for 4h; Reflux;	47%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane

: 84-26-4
rutaecarpine

: 127819-78-7
2-<2-(3-Vinylindolyl)>-4(3H)-quinazolinone

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 100 - 105℃; for 22h;	68%

Rutaecarpine Specification

The systematic name of Rutaecarpine is 8,13-dihydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one. With the CAS registry number 84-26-4, it is also named as Indolo(2',3':3,4)pyrido(2,1-b)quinazolin-5(7H)-one, 8,13-dihydro- (9CI). The product's category is Indoles and Derivatives. Besides, it is white solid, which should be stored at 2-8 °C. In addition, its molecular formula is C₁₈H₁₃N₃O and molecular weight is 287.32.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.94; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.942; (4)ACD/LogD (pH 7.4): 2.943; (5)ACD/BCF (pH 5.5): 101.282; (6)ACD/BCF (pH 7.4): 101.573; (7)ACD/KOC (pH 5.5): 948.005; (8)ACD/KOC (pH 7.4): 950.731; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.792; (13)Molar Refractivity: 83.67 cm³; (14)Molar Volume: 197.275 cm³; (15)Surface Tension: 62.493 dyne/cm; (16)Density: 1.456 g/cm³; (17)Flash Point: 286.473 °C; (18)Melting Point: 260 °C; (19)Solubility: DMSO: 18 mg/mL; (20)Enthalpy of Vaporization: 83.006 kJ/mol; (21)Boiling Point: 550.072 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of Rutaecarpine: this chemical can be prepared by 3-(2-Indol-3-yl-ethyl)-1H-quinazoline-2,4-dione.

This reaction needs POCl₃ and CH₂Cl₂ at temperature of 60 °C. The reaction time is 3 hours. The yield is 40 %.

Uses of Rutaecarpine: it can be used to produce 2-(3-Vinyl-1H-indol-2-yl)-3H-quinazolin-4-one.

This reaction needs NaH and Dimethylformamide at temperature of 100-105 °C for 22 hours. The yield is 68 %.

When you are using this chemical, please be cautious about it as the following: it is toxic if swallowed. In case of accident or if you feel unwell, please seek medical advice immediately (show label where possible).

People can use the following data to convert to the molecule structure.
(1)SMILES: c1ccc2c(c1)c3c([nH]2)-c4nc5ccccc5c(=O)n4CC3
(2)InChI: InChI=1/C18H13N3O/c22-18-13-6-2-4-8-15(13)20-17-16-12(9-10-21(17)18)11-5-1-3-7-14(11)19-16/h1-8,19H,9-10H2
(3)InChIKey: ACVGWSKVRYFWRP-UHFFFAOYAZ
(4)Std. InChI: InChI=1S/C18H13N3O/c22-18-13-6-2-4-8-15(13)20-17-16-12(9-10-21(17)18)11-5-1-3-7-14(11)19-16/h1-8,19H,9-10H2
(5)Std. InChIKey: ACVGWSKVRYFWRP-UHFFFAOYSA-N

Product Name

Rutaecarpine

Synthetic route

Rutaecarpine Specification

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