Formic Acid → 1-(2-Methylphenyl)ethan-1-amine

HRID 2293133Notes

Reaction equation

HRID 2293133 reaction equation
CC[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[CH:11]([NH2:13])=O.[CH:14](O)=O>>[CH3:3][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]([NH2:13])[CH3:14]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 713FormamideHCID 71481-Phenyl-1-propanone

Product 1

HCID 33910421-(2-Methylphenyl)ethan-1-amine

Procedure

26 ml of 2-methylacetophenone(0.2M), 32 ml of formamide and 7.5 ml of formic acid were mixed and reacted at 160° C. for 5 hours while distilling water off. The resultant was cooled to room temperature and extracted from ethyl ether. The extract was washed with water, concentrated under a reduced pressure, added with 20 ml of concentrated hydrochloric acid and heated under reflux for an hour. The reaction solution was cooled to room temperature, washed with ethyl ether and neutralized with aqueous NaOH solution. After extracting the resultant with ethyl ether, the extract was dried over anhydrous sodium sulfate and concentrated under a reduced pressure, to give 16.9 g of the title compound.

Workup

  1. customreacted at 160° C. for 5 hours
  2. distillationwhile distilling water off
  3. extractionextracted from ethyl ether
  4. washThe extract was washed with water
  5. concentrationconcentrated under a reduced pressure
  6. additionadded with 20 ml of concentrated hydrochloric acid
  7. temperatureheated
  8. temperatureunder reflux for an hour
  9. temperatureThe reaction solution was cooled to room temperature
  10. washwashed with ethyl ether and neutralized with aqueous NaOH solution
  11. extractionAfter extracting the resultant with ethyl ether
  12. dry with materialthe extract was dried over anhydrous sodium sulfate
  13. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-94bf087f51ed4180845a77c9cf489724
Source dataset
uspto-grants-1997_11
Patent number
US05686458

Reaction notes

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