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

HRID 1767511Notes

Reaction equation

HRID 1767511 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 96%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-chloro-2-nitrobenzoic acid (20 g, 110 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-eb35f7f8e3a9416eb8f2bad822773dd1
Source dataset
uspto-grants-2007_06
Patent number
US07235546B2

Reaction notes

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