Methanol → Methyl 3-aminocinnamate

HRID 400088Notes

Reaction equation

HRID 400088 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[CH:7]=[CH:8][C:9]([OH:11])=[O:10])([O-])=O.[CH3:15]O.S(=O)(=O)(O)O>O>[NH2:1][C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[CH:7]=[CH:8][C:9]([O:11][CH3:15])=[O:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 683902-Propenoic acid, 3-(3-nitrophenyl)-

Product 1

HCID 54385173Methyl 3-aminocinnamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

While mixing and stirring 193 g of 3-nitrocinnamic acid, 2 of methanol and 50 g of concentrated sulfuric acid, the mixture was heated under reflux for 2 hours. The reaction solution was poured into water and the crystals obtained were filtered. To a reaction solution under heat-refluxing while mixing and stirring 2 of 2-propanol, 200 ml of water, 20 g of ammonium chloride and 200 g of reduced iron, the crystals obtained above were gradually added, and the solution was further heated under reflux for one hour. The reaction solution still being hot was filtered, the filtrate was poured into 10 of water, and the crystals (methyl 3-aminocinnamate) obtained were collected by filtration. Yield: 108 g.

Workup

  1. additionWhile mixing
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. customthe crystals obtained
  5. filtrationwere filtered
  6. temperatureTo a reaction solution under heat-refluxing
  7. additionwhile mixing
  8. customthe crystals obtained
  9. additionabove were gradually added
  10. temperaturethe solution was further heated
  11. temperatureunder reflux for one hour
  12. filtrationThe reaction solution still being hot was filtered
  13. additionthe filtrate was poured into 10 of water

Sources & evidence

ORD record
ord-8c73c921353749408d75b936532bd28c
Source dataset
uspto-grants-1998_10
Patent number
US05827638

Reaction notes

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