Hydrochloric Acid → 6-Acetyl-4-chloro-3'-fluoro-3-methylbiphenyl-2-carboxamide

HRID 510822Notes

Reaction equation

HRID 510822 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([Cl:20])[C:7]([CH3:19])=[C:8]([C:17]#[N:18])[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)(=[O:3])[CH3:2].[OH-:21].[K+].Cl>C(O)C>[C:1]([C:4]1[CH:5]=[C:6]([Cl:20])[C:7]([CH3:19])=[C:8]([C:17]([NH2:18])=[O:21])[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 583684696-Acetyl-4-chloro-3'-fluoro-3-methylbiphenyl-2-carbonitrile

Product 1

HCID 866667626-Acetyl-4-chloro-3'-fluoro-3-methylbiphenyl-2-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-acetyl-4-chloro-3′-fluoro-3-methylbiphenyl-2-carbonitrile (0.87 g, 3.0 mmol) and potassium hydroxide (0.34 g, 6.1 mmol) in ethanol (4 mL) was refluxed for 2 hours. The mixture was cooled, 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 to yield the crude product. LCMS calculated for C16H14ClFNO2 (M+H)+: m/z=306.1. found: 306.0.

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureThe mixture was 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

Sources & evidence

ORD record
ord-20d449cd2b9846cbaa0a96ccd8340865
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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