9-Nitro-1,7-diphenyl-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinoline → 1,7-Diphenyl-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-amine

HRID 1972118Notes

Reaction equation

HRID 1972118 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11]3=[C:12]([CH:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH2:15][CH2:16][N:10]3[CH2:9][CH2:8][CH:7]2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:13]=1)([O-])=O>CO.[Pd]>[C:23]1([CH:7]2[C:6]3[C:11]4=[C:12]([CH:14]([C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=5)[CH2:15][CH2:16][N:10]4[CH2:9][CH2:8]2)[CH:13]=[C:4]([NH2:1])[CH:5]=3)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 1

HCID 40410309-Nitro-1,7-diphenyl-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinoline2×

Product 1

HCID 29025301,7-Diphenyl-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 9-nitro-1,7-diphenyl-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinoline (Intermediate 3), (1.2 g, 7.06 mmol), in MeOH (100 mL) was subjected to hydrogenation reaction by the action of 10% Pd/C (120 mg) under H2 balloon at room temperature for 12 h. The mixture was filtered through Celite and freed of solvent under reduced pressure to get 1,7-diphenyl-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-amine (Intermediate 4) as a solid, (1.08 g, 98%).

Workup

  1. filtrationThe mixture was filtered through Celite

Sources & evidence

ORD record
ord-618ef6a9e9f844f79a4920b4cd857f31
Source dataset
uspto-grants-2013_04
Patent number
US08431702B2

Reaction notes

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