Formamide → HCID 3041177, compound

HRID 374886Notes

Reaction equation

HRID 374886 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13](=O)[CH3:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C([NH2:18])=O.[OH-].[Na+]>O>[NH2:18][CH:13]([CH2:12][CH2:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:14]

Participants

5

Reactant 3

HCID 713FormamideHCID 14798Sodium HydroxideHCID 2375614-(3,4-Dimethoxyphenyl)-2-butanone

Product 1

HCID 3041177HCID 3041177, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
210 °C

Procedure

A mixture of 41.4 g of 4-(3,4-dimethoxy-phenyl)-2-butanone and 41.9 ml of formamide is heated at 210° C. for 20 hours, cooled to ambient, 104 ml of 10N sodium hydroxide is added and the reaction mixture heated at reflux temperature for 24 hours. The reaction is cooled, added to 200 ml of water and extracted with diethyl ether. The diethyl ether solution is washed with 10% hydrochloric acid. The aqueous layer is made basic and extracted with diethyl ether. The organic layer is dried, filtered and evaporated in vacuo. The residue is purified by chromatography (silica gel: chloroform/hexane/ethyl acetate to 5% methyl alcohol/chrloroform) to give 5.72 g of racemic 2 -amino-4 -(3,4-dimethoxyphenyl)butane.

Workup

  1. temperaturecooled
  2. temperaturethe reaction mixture heated
  3. temperatureat reflux temperature for 24 hours
  4. temperatureThe reaction is cooled
  5. extractionextracted with diethyl ether
  6. washThe diethyl ether solution is washed with 10% hydrochloric acid
  7. extractionextracted with diethyl ether
  8. customThe organic layer is dried
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customThe residue is purified by chromatography (silica gel: chloroform/hexane/ethyl acetate to 5% methyl alcohol/chrloroform)

Sources & evidence

ORD record
ord-73e3e175da5f417381f6f0a33f79b1fd
Source dataset
uspto-grants-1996_01
Patent number
US05482971

Reaction notes

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