Potassium Hydroxide → HCID 16719743, compound

HRID 1868375Notes

Reaction equation

HRID 1868375 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[C:13]([C:20]([O:22]C)=[O:21])=[CH:12][N:11]=1.[OH-].[K+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:15]=[C:14]([C:16]([F:17])([F:18])[F:19])[C:13]([C:20]([OH:22])=[O:21])=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 167195495-Pyrimidinecarboxylic acid, 2-[(2,4-dichlorophenyl)amino]-4-(trifluoromethyl)-, methyl ester

Product 1

HCID 16719743HCID 16719743, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of methyl 2-(2,4-dichlorophenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylate (107 g) in methanol (700 ml) was added a solution of potassium hydroxide (50 g) in methanol (700 ml) and the solution stirred at reflux for 24 h. Methanol was removed under reduced pressure and water (800 ml) added. The solution was washed with ether (3×400 ml, which removed the remaining 2,4-dichloroaniline) and concentrated hydrochloric acid added to adjust the acidity to pH 1. The precipitated solid was filtered, washed with 2N HCl and water until the pH of the filtrate was neutral. The solid was dried in vacuo at 50° C. to afford 2-(2,4-dichlorophenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylic acid (86.9 g)

Workup

  1. temperatureat reflux for 24 h
  2. customMethanol was removed under reduced pressure and water (800 ml)
  3. additionadded
  4. washThe solution was washed with ether (3×400 ml, which
  5. customremoved the remaining 2,4-dichloroaniline) and concentrated hydrochloric acid
  6. additionadded
  7. filtrationThe precipitated solid was filtered
  8. washwashed with 2N HCl and water until the pH of the filtrate
  9. customThe solid was dried in vacuo at 50° C.

Sources & evidence

ORD record
ord-b4810d6dcd804e6a82f01ad7e17e63f8
Source dataset
uspto-grants-2009_12
Patent number
US07635701B2

Reaction notes

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