HCID 67021355, compound → HCID 67021538, compound

HRID 1660936Notes

Reaction equation

HRID 1660936 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N+:18]([O-])=O)=[CH:7][CH:6]=1>CO.[Ni]>[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[NH2:18])=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 67021355HCID 67021355, compound

Product 1

HCID 67021538HCID 67021538, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-chloro-3-nitropyridine (0.500 g, 3.06 mmol) (LANCASTER) and (4-aminophenyl)-acetic acid (0.467 g 3.06 mmol) (Aldrich) in MeOH/dioxane (10 mL, 1/1 v/v) is stirred and refluxed for 6 h. The mixture is allowed to cool to rt and concentrated in vacuo to afford crude [4-(3-nitro-pyridin-4-ylamino)-phenyl]-acetic acid methyl ester. A suspension of the crude ester (0.569 g) and Raney Ni (˜0.140 g) in MeOH (15 mL) is stirred for 21 h at rt, under a hydrogen atmosphere. The reaction mixture is filtered through a pad of Celite and concentrated. Trituration of the residue in CH2Cl2 affords the title compound as a beige solid: ES-MS: 258.0 [M+H]+; single peak at tR=2.54 min (System 1).

Workup

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

Sources & evidence

ORD record
ord-d3417ac1fa4d40c9a09cb0b46661c545
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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