4-Methylbenzaldehyde → HCID 85069354, compound

HRID 352536Notes

Reaction equation

HRID 352536 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:13][NH2:14])=[O:12])=[C:5]2[CH3:15].[C:16]1([CH3:24])[CH:21]=[CH:20][C:19]([CH:22]=O)=[CH:18][CH:17]=1>C(O)C>[CH3:24][C:16]1[CH:21]=[CH:20][C:19]([CH:22]=[N:14][NH:13][C:11]([C:6]2[NH:7][C:8]3[C:4]([C:5]=2[CH3:15])=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=3)=[O:12])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 77254-MethylbenzaldehydeHCID 12512450HCID 12512450, compound

Product 1

HCID 85069354HCID 85069354, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-chloro-3-methyl-indole-2-carboxylic acid hydrazide (13 mg, 0.054 mmol),p-tolualdehyde (6.5 mg, 0.054 mmol) in ethanol (5 mL) was refluxed for 8 h. It was evaporated in vacuo and the residue was purified by column chromatography (silica gel, EtOAc/Hexane=4:1) to give 7.8 mg (42%) of the title compound. 1H NMR (CD3OD): 8.26 (s, 1H), 7.72 (d, J=8.1 Hz, 2H), 7.62 (bs, 1H), 7.39 (d, J=8.7 Hz, 1H), 7.28−7.21 (m, 3H), 2.58 (s, 3H), 2.39 (s, 3H).

Workup

  1. customIt was evaporated in vacuo
  2. customthe residue was purified by column chromatography (silica gel, EtOAc/Hexane=4:1)

Sources & evidence

ORD record
ord-44a76112a8df4c8ea07be593e5b54c6d
Source dataset
uspto-grants-2004_06
Patent number
US06747052B2

Reaction notes

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