Indole-3-Carboxaldehyde → HCID 57262957, compound

HRID 1825735Notes

Reaction equation

HRID 1825735 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[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH:24]=O)=[CH:16]1>CN(C=O)C>[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH:24]=[C:5]2[C:6](=[O:14])[NH:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[O:4]2)=[CH:16]1

Participants

5

Reactant 3

HCID 10256Indole-3-CarboxaldehydeHCID 727572H-1,4-benzoxazin-3(4H)-oneHCID 10942334Sodium Methoxide

Product 1

HCID 57262957HCID 57262957, 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 indole-3-carboxaldehyde (2.32 g, 0.016 mol) in dry DMF (10 ml). The reaction mixture was refluxed for 24 h, then cooled at room temperature and poured into crushed ice and left overnight in the refrigerator. The precipitated solid was collected by filtration, washed with water and dried. The crude product was chromatographed on silica gel using (9:1) toluene:ethyl acetate.

Workup

  1. temperatureThe reaction mixture was refluxed for 24 h
  2. additionpoured
  3. custominto crushed ice
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water
  6. customdried
  7. customThe crude product was chromatographed on silica gel using (9:1) toluene

Sources & evidence

ORD record
ord-fc8d53ad2851453e98de251fef1d0dc4
Source dataset
uspto-grants-2006_05
Patent number
US07049312B1

Reaction notes

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