Pyrrole-2-carboxaldehyde → HCID 69637174, compound

HRID 1825743Notes

Reaction equation

HRID 1825743 reaction equation
C[O-].[Na+].[O:4]1[CH2:9][C:8](=[O:10])[NH:7][C:6]2[N:11]=[CH:12][CH:13]=[CH:14][C:5]1=2.[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:9]1[O:4][C:5]2[CH:14]=[CH:13][CH:12]=[N:11][C:6]=2[NH:7][C:8]1=[O:10]

Participants

5

Reactant 3

HCID 13854Pyrrole-2-carboxaldehydeHCID 884992H-pyrido(3,2-b)-1,4-oxazin-3(4H)-oneHCID 10942334Sodium Methoxide

Product 1

HCID 69637174HCID 69637174, 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-pyrido[3,2-b][1,4]oxazin-3(4H)-one (1.50 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 to room temperature, poured into crushed ice and left overnight at 4° C. The precipitated solid was filtered off, washed with water and dried. The dark solid was boiled with ethanol (150 ml) and filtered hot to remove impurities. The filtrate was evaporated to dryness under reduced pressure, and the residue was purified by silica gel chromatographed 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 filtered off
  5. washwashed with water
  6. customdried
  7. filtrationfiltered hot
  8. customto remove impurities
  9. customThe filtrate was evaporated to dryness under reduced pressure
  10. customthe residue was purified by silica gel
  11. customchromatographed

Sources & evidence

ORD record
ord-8951838f647d46eaadf88099bcfe752f
Source dataset
uspto-grants-2006_05
Patent number
US07049312B1

Reaction notes

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