N-(2-Chlorophenyl)-6-methoxy-3-nitro-4-quinolinamine → HCID 60046938, compound

HRID 1672327Notes

Reaction equation

HRID 1672327 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=2)[N:12]=[CH:11][C:10]=1[N+:21]([O-])=O>CO.[Ni]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=2)[N:12]=[CH:11][C:10]=1[NH2:21]

Participants

4

Reactant 1

HCID 60046940N-(2-Chlorophenyl)-6-methoxy-3-nitro-4-quinolinamine

Product 1

HCID 60046938HCID 60046938, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

The title compound is prepared in analogy to Example 19e, starting from 0.8 g (2.4 mmol) of (2-chloro-phenyl)-(6-methoxy-3-nitro-quinolin-4-yl)-amine (Example 44h) and 0.4 g Raney-Ni in 30 ml methanol. Time of hydrogenation: 1 h at rt. Crystallization of the product from ethyl acetate-hexane. mp: 120-123° C.; MS: 300 (M++1); HPLC: tret=8.41 min (Grad 1).

Workup

  1. custom1 h
  2. customat rt
  3. customCrystallization of the product from ethyl acetate-hexane
  4. customtret=8.41 min (Grad 1)

Sources & evidence

ORD record
ord-631462b395b845c7821cec9167f6e423
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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