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(8-Nitro-quinolin-7-ylmethyl)-phenyl-amine → 7-Phenylaminomethyl-quinolin-8-ylamine

HRID 513646
Notes
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Reaction equation

HRID 513646 reaction equation
[N+:1]([C:4]1[C:5]([CH2:14][NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-])=O>[Pd].CCO.CO>[C:16]1([NH:15][CH2:14][C:5]2[C:4]([NH2:1])=[C:13]3[C:8]([CH:9]=[CH:10][CH:11]=[N:12]3)=[CH:7][CH:6]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 68183055(8-Nitro-quinolin-7-ylmethyl)-phenyl-amine2×

Product 1

HCID 681831547-Phenylaminomethyl-quinolin-8-ylamineYield 101.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Palladium on Carbon (10%, 36 mg) was added to a solution of (8-nitro-quinolin-7-ylmethyl)-phenyl-amine (Intermediate 205) (478 mg, 1.69 mmol) in EtOH (10 ml) and the mixture was stirred under an atmosphere of hydrogen for 4 h. The mixture was diluted with MeOH (40 ml), filtered through celite and the filtrate was concentrated in vacuo to give the title compound (428 mg, 89%).

Workup

  1. filtrationfiltered through celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5dc7a3364bbe47689bcf94fa6c9e5ac0
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09102688B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes