Methyl 2-chloro-3-nitrobenzoate → Methyl 3-amino-2-chlorobenzoate

HRID 1961774Notes

Reaction equation

HRID 1961774 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>CO.[Ni]>[NH2:12][C:11]1[C:2]([Cl:1])=[C:3]([CH:8]=[CH:9][CH:10]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 1

HCID 10751184Methyl 2-chloro-3-nitrobenzoate

Product 1

HCID 15132848Methyl 3-amino-2-chlorobenzoateYield 320.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of methyl 2-chloro-3-nitrobenzoate (25 g, 116 mmol) in MeOH (150 mL) was added Raney Ni (3 g). The mixture was stirred under H2 atmosphere (50 psi at 25° C.) for 3.5 h. The catalyst was filtered, and the filtrate was concentrated under the reduced pressure to dryness to give the crude product, which was purified by recrystallization in EtOAc to afford the title compound (69 g, 83.5% yield, four batches combined). 1H NMR (400 MHz, CDCl3) δ ppm 6.70-7.25 (m, 3H), 4.40-4.50 (br, 2H), 3.87 (s, 3H).

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated under the reduced pressure to dryness
  3. customto give the crude product, which
  4. customwas purified by recrystallization in EtOAc

Sources & evidence

ORD record
ord-c319d57653b64123929629c411dc294a
Source dataset
uspto-grants-2013_04
Patent number
US08415345B2

Reaction notes

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