Methyl 4-cyano-2-fluorobenzoate → Methyl 4-(aminomethyl)-2-fluorobenzoate

HRID 2355277Notes

Reaction equation

HRID 2355277 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][C:5]=1[F:12]>[Ni].C(O)C.N.CO>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH2:11])=[CH:6][C:5]=1[F:12]

Participants

6

Reactant 1

HCID 15278726Methyl 4-cyano-2-fluorobenzoate

Product 1

HCID 57572260Methyl 4-(aminomethyl)-2-fluorobenzoate

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Add a slurry of Raney nickel in ethanol (1.2 g, 1.2 ml) to 4-cyano-2-fluoro-benzoic acid methyl ester (5.8 g, 30.0 mmol) in 2N ammonia in methanol (580 mL). Purge with nitrogen gas (3×), purge with hydrogen gas (3×), and pressurize with hydrogen gas to 419 KPa. Heat the reaction at 40° C. for 18 hrs. Allow to cool to room temperature and filter the reaction mixture. Concentrate the filtrate to the crude title compound (6.9 g, 99%). MS (m/z): 184 (M+1).

Workup

  1. customPurge with nitrogen gas (3×)
  2. custompurge with hydrogen gas (3×)
  3. temperatureHeat
  4. customthe reaction at 40° C. for 18 hrs
  5. filtrationfilter the reaction mixture
  6. concentrationConcentrate the filtrate to the crude title compound (6.9 g, 99%)

Sources & evidence

ORD record
ord-2b70e9e0adf044809aa57f7dd10d3379
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

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