Hydrochloric Acid → N-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxy-5-(1-hydroxyethyl)benzamide

HRID 2384352Notes

Reaction equation

HRID 2384352 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:27])=[C:8]([CH:26]=1)[C:9]([NH:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14]([C:22]([F:25])([F:24])[F:23])[CH:13]=1)=[O:10])(=[O:3])[CH3:2].[BH4-].[Na+].Cl>C(O)C>[F:19][C:18]([F:20])([F:21])[C:16]1[CH:17]=[C:12]([NH:11][C:9](=[O:10])[C:8]2[CH:26]=[C:4]([CH:1]([OH:3])[CH3:2])[CH:5]=[CH:6][C:7]=2[OH:27])[CH:13]=[C:14]([C:22]([F:24])([F:25])[F:23])[CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 103857615-acetyl-N-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxybenzamide

Product 1

HCID 11338361N-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxy-5-(1-hydroxyethyl)benzamideYield 78.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Acetyl-N-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxybenzamide (50.5 mg, 0.13 mmol) was suspended in ethanol (2 mL). Sodium borohydride (23.6 mg, 0.62 mmol) was added, and the mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation under reduced pressure was washed with isopropyl ether/n-hexane under suspension to give the title compound (39.7 mg, 78.3%) as white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe residue obtained by evaporation under reduced pressure
  5. washwas washed with isopropyl ether/n-hexane under suspension

Sources & evidence

ORD record
ord-1315fe950d8140b1b3dcaf93f1cccb15
Source dataset
uspto-grants-2012_09
Patent number
US08263657B2

Reaction notes

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