Benzoic acid, 3-amino-, methyl ester → Methyl 3-[(3-ethoxyacryloyl)amino]benzoate

HRID 483154Notes

Reaction equation

HRID 483154 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH2:12]([O:14][CH:15]=[CH:16][C:17](Cl)=[O:18])[CH3:13]>C(OCC)C>[CH3:8][O:7][C:5]([C:4]1[CH:3]=[C:2]([CH:11]=[CH:10][CH:9]=1)[NH:1][C:17](=[O:18])[CH:16]=[CH:15][O:14][CH2:12][CH3:13])=[O:6]

Participants

4

Reactant 2

HCID 78274Benzoic acid, 3-amino-, methyl esterHCID 30144293-Ethoxy-2-propenoyl chloride

Product 1

HCID 53940533Methyl 3-[(3-ethoxyacryloyl)amino]benzoateYield 63.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution containing 29.5 g of methyl m-aminobenzoate in 300 ml of diethyl ether, 11.53 g of β-ethoxyacrylic acid chloride was added dropwise at 17°-27° C. under stirring condition. After the addition was finished, the reaction mixture was further stirred at a room temperature for 1 hour, then the crystals thus precipitated were collected by filtration. The crystals were washed with ether, and the crude crystals were dissolved in chloroform, then the chloroform solution was washed with 0.5N-hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride. The chloroform solution was dried and then chloroform was removed by distillation, and the residue thus obtained was purified by a silica gel column chromatography, then recrystallized from methanol to obtain 13.63 g of m-methoxycarbonyl-N-(β-ethoxyacryloyl)aniline in the form of colorless prism-like crystals.

Workup

  1. additionwas added dropwise at 17°-27° C.
  2. additionAfter the addition
  3. stirringthe reaction mixture was further stirred at a room temperature for 1 hour
  4. customthe crystals thus precipitated
  5. filtrationwere collected by filtration
  6. washThe crystals were washed with ether
  7. dissolutionthe crude crystals were dissolved in chloroform
  8. washthe chloroform solution was washed with 0.5N-hydrochloric acid
  9. dry with materialThe chloroform solution was dried
  10. customchloroform was removed by distillation
  11. customthe residue thus obtained
  12. customwas purified by a silica gel column chromatography
  13. customrecrystallized from methanol

Sources & evidence

ORD record
ord-c4eac3ef3ffe4faa8188323084c2da23
Source dataset
uspto-grants-1986_03
Patent number
US04578381

Reaction notes

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