Formic Acid → N-[2-(7-methoxy-1,3-benzodioxol-5-yl)ethyl]formamide

HRID 1253109Notes

Reaction equation

HRID 1253109 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH2:13][CH2:14][NH-:15])[CH:7]=[C:8]2[O:12][CH2:11][O:10][C:9]=12.[OH-].[Na+].[CH:18](O)=[O:19]>O>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH2:13][CH2:14][NH:15][CH:18]=[O:19])[CH:7]=[C:8]2[O:12][CH2:11][O:10][C:9]=12

Participants

5

Reactant 3

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 867421922-(3-Methoxy-4,5-methylenedioxyphenyl)ethylamide hydrochloride

Product 1

HCID 10198394N-[2-(7-methoxy-1,3-benzodioxol-5-yl)ethyl]formamideYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6.95 g (30 mmol) of 2-(3-methoxy-4,5-methylenedioxyphenyl)ethylamide hydrochloride was dissolved in 30 ml of water, and the mixture was made basic with 25% sodium hydroxide aqueous solution. The mixture was extracted with 30 ml of toluene. The toluene layer was washed with 10 ml of water, added with 2.73 g (59.3 mmol) of formic acid, refluxed under heating for 2 hours at normal pressure to distill off about 15 ml of the toluene while separating the produced water by an azeotropic distillation and then cooled. The deposited crystal was filtered out, washed with 3 ml of toluene and dried to obtain 5.48 g of N-[2-(3-methoxy-4,5-methylenedioxyphenyl)ethyl]formamide (C). Yield: 83%; melting point: 108°-110° C.

Workup

  1. extractionThe mixture was extracted with 30 ml of toluene
  2. washThe toluene layer was washed with 10 ml of water
  3. temperaturerefluxed
  4. temperatureunder heating for 2 hours at normal pressure
  5. distillationto distill off about 15 ml of the toluene
  6. customwhile separating the produced water
  7. distillationby an azeotropic distillation
  8. temperaturecooled
  9. filtrationThe deposited crystal was filtered out
  10. washwashed with 3 ml of toluene
  11. customdried

Sources & evidence

ORD record
ord-0c793d2906a54f72b6fcb4757a104709
Source dataset
uspto-grants-1988_05
Patent number
US04746747

Reaction notes

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