Hydrochloric Acid → 2-Amino-1-[4-fluoro-3-(trifluoromethyl)phenyl]ethanone Hydrochloride

HRID 2194476Notes

Reaction equation

HRID 2194476 reaction equation
C1N2CN3[CH2:10][N:4](C2)CN1C3.[F:11][C:12]1[CH:21]=[CH:20][C:15]([C:16](=[O:19])CBr)=[CH:14][C:13]=1[C:22]([F:25])([F:24])[F:23].C(OCC)(=O)C.C(O)C.[ClH:35]>>[ClH:35].[NH2:4][CH2:10][C:16]([C:15]1[CH:20]=[CH:21][C:12]([F:11])=[C:13]([C:22]([F:25])([F:23])[F:24])[CH:14]=1)=[O:19]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 4101HexamethylenetetramineHCID 8857Ethyl AcetateHCID 27787872-Bromo-4'-fluoro-3'-(trifluoromethyl)acetophenone

Product 1

HCID 666499872-Amino-1-[4-fluoro-3-(trifluoromethyl)phenyl]ethanone HydrochlorideYield 100%

Procedure

Add methenamine (1.10 equiv; 231.55 mmoles; 32.46 g) to a solution of 4-fluoro-3-(trifluoromethyl)phenacyl bromide (60.00 g; 1.00 equiv; 210.50 mmoles) in ethyl acetate (450 mL; 4.60 moles). Stir the mixture at RT overnight. Remove the solvent in vacuo and triturate the solid in methyl tert-butyl ether (MTBE). Filter and dry under reduced pressure. Add ethanol (450 mL; 7.73 moles), followed by hydrogen chloride (150 mL; 8.30 equiv; 1.75 moles) and stir the mixture at RT overnight. Remove the solvent in vacuo and dry the solid in vacuo at 50° C. for a week to obtain 2-Amino-1-(4-fluoro-3-trifluoromethyl-phenyl)-ethanone hydrochloride (54.23 g; 100% yield) as a white solid.

Workup

  1. customRemove the solvent in vacuo
  2. customtriturate the solid in methyl tert-butyl ether (MTBE)
  3. filtrationFilter
  4. customdry under reduced pressure
  5. stirringstir the mixture at RT overnight
  6. customRemove the solvent in vacuo
  7. customdry the solid in vacuo at 50° C. for a week

Sources & evidence

ORD record
ord-a8967d20d0ba4e328e7fc7e65bc2343b
Source dataset
uspto-grants-2012_12
Patent number
US08334293B2

Reaction notes

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