Pyrrole-2-carboxaldehyde → HCID 57122936, compound

HRID 1825734Notes

Reaction equation

HRID 1825734 reaction equation
C[O-].[Na+].[O:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6](=[O:14])[CH2:5]1.[NH:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[CH:20]=O>CN(C=O)C>[NH:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[CH:20]=[C:5]1[C:6](=[O:14])[NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:4]1

Participants

5

Reactant 3

HCID 13854Pyrrole-2-carboxaldehydeHCID 727572H-1,4-benzoxazin-3(4H)-oneHCID 10942334Sodium Methoxide

Product 1

HCID 57122936HCID 57122936, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium methoxide (0.65 g, 0.012 mol) was added in one portion to a mixture of 2H-1,4-benzoxazin-3(4H)-one (1.49 g, 0,01 mol) and pyrrole-2-carboxaldehyde (1.58 g, 0.016 mol) in dry DMF (10 ml). The reaction mixture was refluxed for 48 h, then cooled at room temperature and poured into crushed ice and left overnight at 4° C. The precipitated solid was collected by filtration, washed with water and dried. The precipitate was boiled with ethanol (150 ml) and filtered while hot to remove impurities. The filtrate was evaporated to dryness under reduced pressure, and the residue was chromatographed on a silica gel column using (95:5) toluene:ethyl acetate as the mobile phase.

Workup

  1. temperatureThe reaction mixture was refluxed for 48 h
  2. additionpoured
  3. custominto crushed ice
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water
  6. customdried
  7. filtrationfiltered while hot
  8. customto remove impurities
  9. customThe filtrate was evaporated to dryness under reduced pressure
  10. customthe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-84192316f7054b238ca62b0d871af65e
Source dataset
uspto-grants-2006_05
Patent number
US07049312B1

Reaction notes

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