Hydrochloric Acid → HCID 67970562, compound

HRID 889535Notes

Reaction equation

HRID 889535 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:13]([F:15])[F:14])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])#[N:2].[ClH:16].[H][H]>[Pd].CO>[ClH:16].[NH2:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([CH:13]([F:14])[F:15])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 67970696HCID 67970696, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67970562HCID 67970562, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Purge a mixture of methyl 5-cyano-2-(difluoromethyl)benzoate (9.37 g, 44.4 mmol, 1.0 equiv), palladium (10% on carbon, 3.00 g, 2.82 mmol, 0.064 equiv), and methanol (50 mL) with nitrogen, then add hydrochloric acid (37 wt % aqueous, 8.0 mL, 105.6 mmol, 2.38 equiv), and stir the resulting suspension under 275 kPaG of hydrogen at room temperature overnight. Remove the solids by filtration, concentrate the filtrate under reduced pressure, and dry the resulting material in a 40° C. vacuum oven overnight to give the title compound as a light brown solid (7.01 g, 83%). MS (m/z) 216 (M+1).

Workup

  1. customPurge
  2. customRemove the solids
  3. filtrationby filtration
  4. concentrationconcentrate the filtrate under reduced pressure
  5. customdry the resulting material in a 40° C. vacuum oven overnight

Sources & evidence

ORD record
ord-d81194d3ad3445abae548a18128aa598
Source dataset
uspto-grants-2012_08
Patent number
US08252831B2

Reaction notes

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