Methyl 3-[(3-ethoxyacryloyl)amino]benzoate → Methyl 2-oxo-1,2-dihydroquinoline-5-carboxylate

HRID 483157Notes

Reaction equation

HRID 483157 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:16]=[CH:17][CH:18]=1)[NH:8][C:9](=[O:15])[CH:10]=[CH:11]OCC)=[O:4]>S(=O)(=O)(O)O>[CH3:1][O:2][C:3]([C:5]1[CH:18]=[CH:17][CH:16]=[C:7]2[C:6]=1[CH:11]=[CH:10][C:9](=[O:15])[NH:8]2)=[O:4]

Participants

3

Reactant 1

HCID 53940533Methyl 3-[(3-ethoxyacryloyl)amino]benzoate

Product 1

HCID 12503491Methyl 2-oxo-1,2-dihydroquinoline-5-carboxylate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

10 Grams of m-methoxycarbonyl-N-(β-ethoxyacryloyl)aniline was added to 100 ml of concentrated sulfuric acid gradually, and this mixture was stirred at a room temperature for 2 hours, then at 45° C. for 4 hours. The reaction mixture was poured in ice-water, and the precipitated crystals were collected by filtration and were washed with water. Thus obtained crude crystals were recrystallized from methanol-chloroform to obtain 6.97 g of 5-methoxycarbonylcarbostyril.

Workup

  1. waitat 45° C. for 4 hours
  2. filtrationthe precipitated crystals were collected by filtration
  3. washwere washed with water
  4. customThus obtained crude crystals
  5. customwere recrystallized from methanol-chloroform

Sources & evidence

ORD record
ord-50f57b2ad3e74b08bc55d59518cdbb16
Source dataset
uspto-grants-1986_03
Patent number
US04578381

Reaction notes

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