Potassium Hydroxide → 2-(3-Chlorophenylamino)-4-trifluoromethylpyrimidine-5-carboxylic acid

HRID 1868369

Reaction equation

HRID 1868369 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[C:12]([C:19]([O:21]CC3C=CC=CC=3)=[O:20])=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[K+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[C:12]([C:19]([OH:21])=[O:20])=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 16719547Benzyl 2-(3-chlorophenylamino)-4-trifluoromethylpyrimidine-5-carboxylate

Product 1

HCID 167196552-(3-Chlorophenylamino)-4-trifluoromethylpyrimidine-5-carboxylic acidYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of benzyl 2-(3-chlorophenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylate (0.50 g) in ethanol (15 ml) was added a solution of potassium hydroxide (205 mg) in ethanol (10 ml) and the solution stirred at reflux for 15 h. Ethanol was removed under reduced pressure and water (15 ml) added. The solution was washed with ether and concentrated hydrochloric acid added to adjust the acidity to pH 1. The precipitated solid was filtered, washed with water and dried in vacuo at 50° C. to afford 2-(3-chlorophenylamino)-4-trifluoromethylpyrimidine-5-carboxylic acid (366 mg).

Workup

  1. temperatureat reflux for 15 h
  2. customEthanol was removed under reduced pressure and water (15 ml)
  3. additionadded
  4. washThe solution was washed with ether and concentrated hydrochloric acid
  5. additionadded
  6. filtrationThe precipitated solid was filtered
  7. washwashed with water
  8. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-0a8863d90b884e32be04b4aec80d7761
Source dataset
uspto-grants-2009_12
Patent number
US07635701B2

Linked notes

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