Sodium Methoxide → 10-methyl-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione

HRID 1287572Notes

Reaction equation

HRID 1287572 reaction equation
[CH3:1][NH:2][C:3]1[C:4](=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:5]([N:7]1[CH2:14][CH2:13][CH2:12][C@H:8]1[C:9](O)=[O:10])=[O:6].C[O-].[Na+]>C(O)C>[CH3:1][N:2]1[C:3]2[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=2[C:5](=[O:6])[N:7]2[CH2:14][CH2:13][CH2:12][CH:8]2[C:9]1=[O:10]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 227914541-[2-(Methylamino)benzoyl]-L-proline

Product 1

HCID 985943610-methyl-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ten grams of the ethyl ester of 1-(N-methylanthraniloyl)proline is dissolved in 100 ml. of ethanol and 3.0 g. of sodium methylate is added. The reaction mixture is heated at reflux temperature for 8 hours and concentrated to remove the solvent. The residue is shaken with benzene and the benzene solution is washed twice with water and concentrated. The residue is purified by recrystallization from ethyl acetate.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux temperature for 8 hours
  3. concentrationconcentrated
  4. customto remove the solvent
  5. washthe benzene solution is washed twice with water
  6. concentrationconcentrated
  7. customThe residue is purified by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-f252478c956e4403bd9e7b6a8f32e2b3
Source dataset
uspto-grants-1976_10
Patent number
US03985732

Reaction notes

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