5-Chloro-2-nitrobenzoic acid → 2-Amino-5-chlorobenzoic acid

HRID 970516Notes

Reaction equation

HRID 970516 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-])=O)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]>C(O)C.[Ni]>[NH2:11][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 172865-Chloro-2-nitrobenzoic acid

Product 1

HCID 124762-Amino-5-chlorobenzoic acidYield 932.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-chloro-2-nitrobenzoic acid (20 g, 10 mmol) in ethanol was added freshly activated raney nickel (2 g). The mixture was stirred overnight at room temperature under hydrogen atmosphere. The solution was filtered through celite and evaporated under reduced pressure to yield 16 g (96%) of white solids. 1H NMR (DMSO-d6): δ 6.77 (d, J=8.9 Hz, 1H), 7.24 (dd, J=2.9, 8.9 Hz, 1H), 7.62 (d, J=2.9 Hz, 1H), 8.7 (b, 3H); EIMS: 170 (M−H).

Workup

  1. filtrationThe solution was filtered through celite
  2. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-54d7773edf14423091036360d7665343
Source dataset
uspto-grants-2007_12
Patent number
US07312220B2

Reaction notes

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