HCID 67021636, compound → HCID 67021584, compound

HRID 1661016Notes

Reaction equation

HRID 1661016 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[C:10]([Cl:11])=[CH:9][C:8]([NH:12][C:13]2[C:18]([N+:19]([O-])=O)=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:7][C:6]=1[Cl:22]>CO.[Ni]>[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[C:10]([Cl:11])=[CH:9][C:8]([NH:12][C:13]2[C:18]([NH2:19])=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:7][C:6]=1[Cl:22]

Participants

4

Reactant 1

HCID 67021636HCID 67021636, compound

Product 1

HCID 67021584HCID 67021584, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of [2,6-dichloro-4-(3-nitro-pyridin-2-ylamino)-phenyl]-acetic acid methyl ester (5 g, 14.0 mmol) and Raney Ni (˜1 g) in MeOH (100 mL) is stirred for 20 h at rt, under a hydrogen atmosphere. The reaction mixture is filtered through a pad of celite and concentrated to afford the title compound as a grey solid: ES-MS: 326.0/328.0 [M+H]+; tR=3.09 min (System 1); TLC: Rf=0.42 (CH2Cl2/MeOH, 95:5).

Workup

  1. filtrationThe reaction mixture is filtered through a pad of celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-b245cca8a65e47288eaad5f5b84f6de1
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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