Hydrochloric Acid → HCID 90020647, compound

HRID 2200141Notes

Reaction equation

HRID 2200141 reaction equation
[BH4-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]([C:16](=[O:18])[CH3:17])[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)([O-:5])=[O:4].Cl>CO>[N+:3]([C:6]1[CH:7]=[C:8]([CH:16]([OH:18])[CH3:17])[CH:9]=[C:10]([C:12]([F:13])([F:14])[F:15])[CH:11]=1)([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 534027751-[3-Nitro-5-(trifluoromethyl)phenyl]ethanone

Product 1

HCID 90020647HCID 90020647, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add sodium borohydride (95 mg, 2.44 mmol) to a solution of 1-(3-nitro-5-(trifluoromethyl)phenyl)ethanone (570 mg, 2.44 mmol) in methanol (5 mL), stir the mixture for 15 min at ambient temperature. Quench the reaction with water, adjust pH=7 with 1N hydrochloric acid, extract with ethyl acetate (50 mL×3), combine the organic layers, wash with brine, dry over sodium sulfate. Concentrate under reduced pressure to provide the crude product. Purify by flash chromatography (silica gel, EtOAc:PE=1:10) to afford the title compound (520 mg, 91.2%).

Workup

  1. customQuench
  2. customthe reaction with water
  3. extractionextract with ethyl acetate (50 mL×3)
  4. washwash with brine
  5. dry with materialdry over sodium sulfate
  6. concentrationConcentrate under reduced pressure
  7. customto provide the crude product
  8. customPurify by flash chromatography (silica gel, EtOAc:PE=1:10)

Sources & evidence

ORD record
ord-d1fb88e606eb41778be31f98c05b9c4d
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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