Ammonium formate → Methyl 3-amino-2-chlorobenzoate

HRID 1466102Notes

Reaction equation

HRID 1466102 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].C([O-])=O.[NH4+]>CO.C1COCC1.C(O)(=O)C.[Zn]>[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

7

Reactant 2

HCID 2723923Ammonium formateHCID 10751184Methyl 2-chloro-3-nitrobenzoate

Product 1

HCID 15132848Methyl 3-amino-2-chlorobenzoate

Reagents, catalysts & solvents 4

HCID 176Acetic AcidCatalystHCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-chloro-3-nitrobenzoate (2.1 g, 9.7 mmol) in methanol (100 mL) and THF (20 mL) was added zinc powder (1.9 g, 29 mmol), ammonium formate (3.1 g, 49 mmol), and a few drops of acetic acid. The mixture was allowed to stir at RT for 18 hours. Most of the volatiles were removed under reduced pressure. The residue was redissolved in EtOAc (200 mL), washed with brine, concentrated and purified by MPLC to provide methyl 3-amino-2-chlorobenzoate.

Workup

  1. customMost of the volatiles were removed under reduced pressure
  2. dissolutionThe residue was redissolved in EtOAc (200 mL)
  3. washwashed with brine
  4. concentrationconcentrated
  5. custompurified by MPLC

Sources & evidence

ORD record
ord-d1f6bd0e943f4087903020be8885380b
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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