Conditions | Yield |
---|---|
With N-Bromosuccinimide; [bis(trifluoroacetoxy)iodo]benzene; sodium nitrite In acetonitrile at 20℃; for 3h; regioselective reaction; | 84% |
Conditions | Yield |
---|---|
Stage #1: 2-nitro-aniline; glycerol With sodium iodide at 20℃; for 0.0833333h; Stage #2: With sulfuric acid for 0.166667h; Cooling with ice; Stage #3: at 140℃; for 2h; | 81% |
Stage #1: 2-nitro-aniline With sulfuric acid at 70 - 80℃; Stage #2: glycerol at 70 - 80℃; Temperature; Further stages; | 79% |
With sulfuric acid In water for 4h; Reflux; | 72% |
8-nitro-1,2,3,4-tetrahydroquinoline
8-nitroquinoline
Conditions | Yield |
---|---|
With iodine; oxygen In 1,2-dichloro-benzene; toluene at 160℃; for 30h; | 77% |
Conditions | Yield |
---|---|
With sulfuric acid In water; glycerol Reflux; | 44% |
Conditions | Yield |
---|---|
Stage #1: quinoline With sulfuric acid; nitric acid at 20℃; for 1h; Stage #2: With sodium carbonate In water | A 34% B 38% |
With sulfuric acid; nitric acid In water at 0 - 20℃; for 1h; | A 35% B n/a |
With sulfuric acid; nitric acid |
Conditions | Yield |
---|---|
durch Nitrieren; |
8-nitroquinoline
Conditions | Yield |
---|---|
With ammonia at 130 - 140℃; im Rohr; |
Conditions | Yield |
---|---|
With phosphoric acid; water; orthoarsenic acid | |
With hydrogenchloride; phosphoric acid In water at 80 - 95℃; for 7h; |
Conditions | Yield |
---|---|
With nitric acid at 160℃; im Rohr; |
8-nitroquinoline
Conditions | Yield |
---|---|
durch Erhitzen ueber den Schmelzpunkt; |
Conditions | Yield |
---|---|
at 160℃; |
quinoline
sulfuric acid
nitric acid
A
8-nitroquinoline
B
5-nitroquinoline
Conditions | Yield |
---|---|
unter Kuehlung; | |
at 0℃; |
quinoline
nitric acid
acetic anhydride
A
8-nitroquinoline
B
3-nitroquinoline
C
6-nitroquinoline
quinoline
acetic anhydride
A
8-nitroquinoline
B
3-nitroquinoline
C
6-nitroquinoline
quinoline
sulfuric acid
nitric acid
A
8-nitroquinoline
B
5-nitroquinoline
C
6,8-dinitroquinoline
D
5,7-dinitroquinoline
Conditions | Yield |
---|---|
in der Hitze; |
Conditions | Yield |
---|---|
beim Eintragen des Chinolin-nitrats; |
sulfuric acid
orthoarsenic acid
2-nitro-aniline
glycerol
8-nitroquinoline
sulfuric acid
nitrobenzene
2-nitro-aniline
glycerol
8-nitroquinoline
Conditions | Yield |
---|---|
at 140℃; im geschlossenen Rohr; |
Conditions | Yield |
---|---|
With Ni-modified Beta zeolite In neat (no solvent) for 0.0833333h; Microwave irradiation; Reflux; Green chemistry; | 19.4 %Chromat. |
Conditions | Yield |
---|---|
With graphitic carbon nitride; hydrazine hydrate In water at 70℃; for 24h; Irradiation; Sealed tube; Green chemistry; chemoselective reaction; | 100% |
With hydrogen In water at 60℃; under 760.051 Torr; for 3h; Green chemistry; | 99% |
With hydrogen In tetrahydrofuran; water at 120℃; under 22502.3 Torr; for 6h; Autoclave; | 99% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide In acetic acid for 2h; | 100% |
With N-Bromosuccinimide In acetic acid at 110℃; for 3h; | 81.4% |
With N-Bromosuccinimide In acetic acid at 65 - 70℃; for 6h; Inert atmosphere; | 75% |
8-nitroquinoline
N-(quinolin-8-yl)hydroxylamine
Conditions | Yield |
---|---|
With 5% rhodium-on-charcoal; hydrazine hydrate In tetrahydrofuran at 0℃; for 4h; Inert atmosphere; | 99% |
With 5% rhodium-on-charcoal; hydrazine hydrate In tetrahydrofuran at 0℃; Inert atmosphere; | 99% |
With ethyl acetate; platinum Hydrogenation; |
8-nitroquinoline
3,6-dibromo-8-nitroquinoline
Conditions | Yield |
---|---|
With N-Bromosuccinimide In acetic acid for 336h; Ambient temperature; | 99% |
8-nitroquinoline
3-iodo-8-nitroquinoline
Conditions | Yield |
---|---|
With N-iodo-succinimide; acetic acid at 100℃; for 3h; | 99% |
With N-iodo-succinimide; acetic acid at 62℃; for 22h; | 97% |
With N-iodo-succinimide In acetic acid at 62℃; for 22.1667h; | 97% |
8-nitroquinoline
3-chloro-8-nitroquinoline
Conditions | Yield |
---|---|
With N-chloro-succinimide In acetic acid for 2h; | 96% |
With N-chloro-succinimide; acetic acid for 3.5h; Heating; | 34% |
With N-chloro-succinimide; acetic acid at 110℃; for 1h; Inert atmosphere; | 30% |
With sulfur dichloride |
Conditions | Yield |
---|---|
In benzene for 5h; Reflux; | 95% |
In dichloromethane at 0 - 35℃; Inert atmosphere; | 69% |
8-nitroquinoline
1-chloro-N,N-dimethylmethane sulfonamide
N,N-dimethyl-(8-nitro-7-quinolyl)methanesulfonamide
Conditions | Yield |
---|---|
With sodium hydroxide In dimethyl sulfoxide at 20 - 25℃; for 0.5h; | 92% |
Conditions | Yield |
---|---|
With formic acid; triethylamine In water; tert-butyl alcohol at 100℃; for 24h; | 91% |
Conditions | Yield |
---|---|
Stage #1: 8-nitroquinoline With sulfuric acid at 35℃; for 0.416667h; Stage #2: benzene at 65℃; for 0.616667h; Temperature; | 90% |
Conditions | Yield |
---|---|
With tetrahydroxydiboron; 5%-palladium/activated carbon; water In acetonitrile at 80℃; for 24h; | 90% |
With tetrahydroxydiboron; copper diacetate In acetonitrile at 80℃; for 24h; Schlenk technique; chemoselective reaction; | 68% |
Conditions | Yield |
---|---|
With palladium; copper diacetate In N,N-dimethyl-formamide at 120℃; for 8h; Inert atmosphere; regioselective reaction; | 89% |
Conditions | Yield |
---|---|
With palladium; copper diacetate In N,N-dimethyl-formamide at 120℃; for 8h; Inert atmosphere; regioselective reaction; | 89% |
8-nitroquinoline
1-chloro-N,N-dimethylmethane sulfonamide
A
5-(Dimethylaminosulfonylmethyl)-8-nitroquinoline
B
N,N-dimethyl-(8-nitro-7-quinolyl)methanesulfonamide
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at -30 - -25℃; for 0.25h; | A 4% B 88% |
Conditions | Yield |
---|---|
With tetrahydroxydiboron; 5%-palladium/activated carbon; water In acetonitrile at 80℃; for 24h; | 88% |
With tetrahydroxydiboron; copper diacetate In acetonitrile at 80℃; for 24h; Schlenk technique; chemoselective reaction; | 70% |
8-nitroquinoline
5-amino-8-nitroquinoline
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; potassium hydroxide In ethanol at 40 - 60℃; for 2.5h; | 87% |
With potassium hydroxide; hydroxylamine hydrochloride In ethanol at 20℃; for 1h; | 55% |
With hydrogenchloride; potassium hydroxide; ethanol; hydroxylamine |
Conditions | Yield |
---|---|
With tetrahydroxydiboron; 5%-palladium/activated carbon; water In acetonitrile at 80℃; for 24h; | 87% |
With tetrahydroxydiboron; copper diacetate In acetonitrile at 80℃; for 24h; Schlenk technique; chemoselective reaction; | 66% |
Conditions | Yield |
---|---|
With tetrahydroxydiboron; 5%-palladium/activated carbon; water In acetonitrile at 80℃; for 24h; | 86% |
With tetrahydroxydiboron; copper diacetate In acetonitrile at 80℃; for 24h; Schlenk technique; chemoselective reaction; | 82% |
With hydrogen In tetrahydrofuran; water at 110℃; under 37503.8 Torr; for 24h; Autoclave; | 79 %Chromat. |
8-nitroquinoline
Conditions | Yield |
---|---|
With palladium; copper diacetate In N,N-dimethyl-formamide at 120℃; for 8h; Inert atmosphere; regioselective reaction; | 86% |
8-nitroquinoline
chloromethyl phenyl sulfone
A
8-Nitro-7-(phenylsulfonylmethyl)quinoline
B
8-Nitro-5-(phenylsulfonylmethyl)quinoline
Conditions | Yield |
---|---|
With sodium hydroxide In dimethyl sulfoxide at 20 - 25℃; for 0.5h; | A 84% B 12% |
8-nitroquinoline
8-nitro-1,2,3,4-tetrahydroquinoline
Conditions | Yield |
---|---|
With iodine; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In dichloromethane at 20℃; Inert atmosphere; | 84% |
With iron(II) triflate; C13H21N3O2 In chloroform at 40℃; for 4h; Schlenk technique; | 76% |
With ammonia borane; C52H64N12Pd2S4(2+)*2F6P(1-) In dodecane; toluene at 100℃; for 24h; Schlenk technique; Inert atmosphere; regioselective reaction; | 58 %Chromat. |
Conditions | Yield |
---|---|
With sodium hydride; dimethyl sulfoxide; potassium hexacyanoferrate(III) In paraffin oil at 20℃; for 6h; | 84% |
8-nitroquinoline
chloromethyl phenyl sulfone
8-Nitro-7-(phenylsulfonylmethyl)quinoline
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at -30 - -25℃; for 0.25h; | 83% |
8-nitroquinoline
dimethyl amine
Dimethyl phosphite
dimethyl (9-aza-1-(dimethylamino)-5H-2-benzazepin-3-yl)phosphonate
Conditions | Yield |
---|---|
With sodium methylate In methanol at 5 - 10℃; | 81% |
8-nitroquinoline
8-amino-1,2,3,4-tetrahydroquinoline
Conditions | Yield |
---|---|
With hexarhodium hexadecacarbonyl; carbon monoxide; water In 2-methoxy-ethanol at 150℃; under 41188.4 Torr; for 48h; | 81% |
With carbon monoxide; water In 2-methoxy-ethanol at 150℃; under 41188.4 Torr; for 48h; | 81% |
With hydrogen; acetic acid; platinum(IV) oxide at 20℃; under 1034.32 Torr; for 20h; | 79% |
8-nitroquinoline
[2-(acetoxymethyl)prop-2-enyl]trimethylsilane
Conditions | Yield |
---|---|
Stage #1: 8-nitroquinoline With N,N-bis(-1-phenylethyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine; bis(dibenzylideneacetone)-palladium(0) In toluene at 25℃; for 0.0833333h; Inert atmosphere; Sealed tube; Stage #2: [2-(acetoxymethyl)prop-2-enyl]trimethylsilane In toluene at 25℃; for 15h; Inert atmosphere; Sealed tube; | 81% |
8-nitroquinoline
(4-chlorophenoxy)acetonitrile
2-(8-nitroquinolin-7-yl)acetonitrile
Conditions | Yield |
---|---|
With potassium tert-butylate In dimethyl sulfoxide at -16 - 20℃; for 2h; | 80% |
With potassium tert-butylate In tetrahydrofuran at -10℃; for 0.416667h; | 58% |
8-nitroquinoline
2,5-hexanedione
8-(2,5-dimethyl-1H-pyrrol-1-yl)quinoline
Conditions | Yield |
---|---|
With indium; acetic acid In toluene at 80℃; for 24h; Inert atmosphere; | 80% |
With hydrogen In neat (no solvent) at 120℃; under 30003 Torr; for 24h; Autoclave; Green chemistry; chemoselective reaction; | 55% |
1. | mmo-sat 50 µg/plate | MUREAV Mutation Research. 39 (1977),285. | ||
2. | mma-sat 100 nmol/plate | MUREAV Mutation Research. 58 (1978),11. | ||
3. | dnr-sat 350 µg/disc | MUREAV Mutation Research. 39 (1977),285. | ||
4. | orl-rat TD:36,400 mg/kg/2Y-C:CAR,REP | CALEDQ Cancer Letters (Shannon, Ireland). 14 (1981),115. | ||
5. | ipr-mus LDLo:125 mg/kg | CBCCT* “Summary Tables of Biological Tests“ National Research Council Chemical-Biological Coordination Center. 6 (1954),149. |
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