Hydrochloric Acid → 6-Acetyl-4-chloro-3',5'-difluoro-3-methylbiphenyl-2-carboxamide

HRID 510864Notes

Reaction equation

HRID 510864 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([Cl:21])[C:7]([CH3:20])=[C:8]([C:18]#[N:19])[C:9]=1[C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=1)(=[O:3])[CH3:2].[OH-:22].[K+].Cl>C(O)C>[C:1]([C:4]1[CH:5]=[C:6]([Cl:21])[C:7]([CH3:20])=[C:8]([C:18]([NH2:19])=[O:22])[C:9]=1[C:10]1[CH:11]=[C:12]([F:17])[CH:13]=[C:14]([F:16])[CH:15]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 866667936-Acetyl-4-chloro-3',5'-difluoro-3-methylbiphenyl-2-carbonitrile

Product 1

HCID 866667946-Acetyl-4-chloro-3',5'-difluoro-3-methylbiphenyl-2-carboxamideYield 29%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-acetyl-4-chloro-3′,5′-difluoro-3-methylbiphenyl-2-carbonitrile (0.20 g, 0.65 mmol) and potassium hydroxide (0.074 g, 1.3 mmol) in ethanol (0.9 mL) was refluxed for 2 hours. After cooled, the mixture was acidified with 1 N HCl and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and evaporated to dryness under reduced pressure. The crude mixture was purified on silica gel, eluting with 0 to 80% ethyl acetate in hexane, to yield the desired product (61 mg, 29%). LCMS calculated for C16H13ClF2NO2 (M+H)+: m/z=324.1. found: 324.0.

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureAfter cooled
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customThe crude mixture was purified on silica gel
  8. washeluting with 0 to 80% ethyl acetate in hexane

Sources & evidence

ORD record
ord-2c15d3ac0b7648f5a2f31fe81c96bb93
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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