HCID 66880495, compound → HCID 66880269, compound

HRID 476155Notes

Reaction equation

HRID 476155 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-])=O)=[C:5]2[NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([CH3:26])([CH3:25])[C:23]#[N:24])=[CH:18][CH:17]=1>C1COCC1.CO.[Ni]>[NH2:12][C:6]1[CH:7]=[N:8][C:9]2[C:4]([C:5]=1[NH:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]([CH3:25])([CH3:26])[C:23]#[N:24])=[CH:20][CH:21]=1)=[CH:3][C:2]([Cl:1])=[CH:11][CH:10]=2

Participants

4

Reactant 1

HCID 66880495HCID 66880495, compound

Product 1

HCID 66880269HCID 66880269, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

2-(4-(6-Chloro-3-nitroquinolin-4-ylamino)phenyl)-2-methylpropanenitrile (Compound of Preparation F, 5 g, 13.6 mmol) and Raney-Ni (2 g) were shaken in 100 mL of THF-MeOH (1:1) under 25 psi of H2 for 3 hours at RT. After completion of reaction, the catalyst was filtered-off and the filtrate was evaporated to dryness to obtain the title compound. Yield: 3.5 g (66%); 1H NMR (DMSO-d6, 300 MHz): δ 8.599 (s, 1H), 7.892 (s, 1H), 7.816-7.846 (d, 1H, J=9 Hz), 7.655-7.663 (d, 1H, J=2.4), 7.312-7349 (dd, 1H, J=8.7 Hz, 2.4 Hz), 7.233-7.262 (d, 2H, J=8.7 Hz), 6.510-6.538 (d, 2H, J=8.4 Hz), 5.457 (s, 2H), 1.598 (s, 6H); MS: m/z 337 (M+).

Workup

  1. customAfter completion of reaction
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-3ebda8b15bc54f7f878352397215c85c
Source dataset
uspto-grants-2014_01
Patent number
US08637670B2

Reaction notes

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