Formic Acid → 1-(5-Chloro-2-methoxyphenyl)ethanamine

HRID 1910552

Reaction equation

HRID 1910552 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([C:8](=O)[CH3:9])[CH:7]=1.C(O)=O.C([NH2:18])=O>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:8]([NH2:18])[CH3:9])[CH:7]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 713FormamideHCID 2404341-(5-Chloro-2-methoxyphenyl)ethanone

Product 1

HCID 45381491-(5-Chloro-2-methoxyphenyl)ethanamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(5-Chloro-2-methoxyphenyl)ethanone (6.7 g, 36.3 mmol) and formic acid (1.74 g, 27.7 mmol) were heated in formamide (10 mL) at 170° 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 (2.7 g, 40%). 1H NMR (400 MHz, CDCl3): δ 7.39 (d, 1H), 7.26 (q, 1H), 6.81 (d, 1H), 4.62 (m, 1H), 3.84 (s, 3H), 1.69 (d, 3H).

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 (2.7 g, 40%)

Sources & evidence

ORD record
ord-54abd3a22d8e4366a54641f4650ffa43
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Linked notes

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