Sodium Hydroxide → HCID 15085963, compound

HRID 1073268Notes

Reaction equation

HRID 1073268 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.[OH-:13].[Na+].Cl.[NH2:16][CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=1)=O>O.C(O)C>[NH2:16][C:17]1[C:18]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:22][CH:21]=2)=[N:7][C:8]2[C:4]([C:5]=1[C:6]([OH:11])=[O:13])=[CH:3][C:2]([F:1])=[CH:10][CH:9]=2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 2365665-FluoroisatinHCID 222816352-Amino-1-[4-(trifluoromethyl)phenyl]ethan-1-one--hydrogen chloride (1/1)

Product 1

HCID 15085963HCID 15085963, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent3×

Procedure

To a stirred suspension of 4.13 g of 5-fluoroisatin in 36 ml of water was added a solution of 5.62 g of sodium hydroxide in 20 ml of water. The stirred solution was heated to 80°-90° C. and a solution of 8.42 g of 2-amino-1-[4-(trifluoromethyl)phenyl]ethanone, hydrochloride in 61 ml of ethanol and 61 ml of water was added dropwise over 1.5 hours. When addition was complete, the mixture was refluxed for 20 minutes, then the ethanol was distilled off. The mixture was cooled in an ice bath, then filtered through celite. The filtrate was acidified to pH 4 with acetic acid, the solid collected, washed with water and recrystallized from acetonitrile, giving 6.04 g of the desired product as a yellow solid, mp 260°-262° C.

Workup

  1. temperatureThe stirred solution was heated to 80°-90° C.
  2. additionWhen addition
  3. temperaturethe mixture was refluxed for 20 minutes
  4. distillationthe ethanol was distilled off
  5. temperatureThe mixture was cooled in an ice bath
  6. filtrationfiltered through celite
  7. customthe solid collected
  8. washwashed with water
  9. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-1a05fc936201415eba72dac42542ef5f
Source dataset
uspto-grants-1990_11
Patent number
US04968702

Reaction notes

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