Formic Acid → 1-(3-Chlorophenyl)ethan-1-amine

HRID 2425978Notes

Reaction equation

HRID 2425978 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH3:9])[CH:5]=[CH:6][CH:7]=1.C(O)=O.C([NH2:16])=O>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([NH2:16])[CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 713FormamideHCID 149331-(3-Chlorophenyl)ethanone

Product 1

HCID 50061701-(3-Chlorophenyl)ethan-1-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(3-Chlorophenyl)ethanone (11.9 g, 77.5 mmol) and formic acid (3.72 g, 77.5 mmol) were heated in formamide (10 mL) at 170-180° C. for 20 h. The mixture was cooled to room temperature, diluted with water and extracted with benzene. After removal of benzene by rotary evaporation the crude mixture was heated under reflux conditions in 3M HCl for 30 h. After cooling, the reaction was added to ether and extracted. The aqueous layer was basified with NaOH to pH 9 and extracted with dichloromethane. The dichloromethane was evaporated to collect the title compound (3.93 g, 33%). 1H NMR (400 MHz, CDCl3): δ 7.34 (s, 1H), 7.21 (m, 3H), 4.07 (m, 1H), 1.35 (d, 3H); MS (ESI) m/z: Calculated for C8H11ClN: 156.06; Observed: 156.0 (M++1).

Workup

  1. extractionextracted with benzene
  2. customAfter removal of benzene
  3. customby rotary evaporation the crude mixture
  4. temperaturewas heated under reflux conditions in 3M HCl for 30 h
  5. temperatureAfter cooling
  6. additionthe reaction was added to ether
  7. extractionextracted
  8. extractionextracted with dichloromethane
  9. customThe dichloromethane was evaporated
  10. customto collect the title compound (3.93 g, 33%)

Sources & evidence

ORD record
ord-295217b271a545b8854514e8ee0eb8b6
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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