Dimethylformamide → ethyl 3-formyl-1H-indole-2-carboxylate

HRID 24334Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].O=P(Cl)(Cl)Cl.CN([CH:23]=[O:24])C>>[CH2:13]([O:12][C:10]([C:2]1[NH:1][C:9]2[C:4]([C:3]=1[CH:23]=[O:24])=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:11])[CH3:14]

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 24813Phosphorus oxychloride

HCID 73125Ethyl indole-2-carboxylate

Product 1

HCID 5107764ethyl 3-formyl-1H-indole-2-carboxylate

Procedure

Ethyl indole-2-carboxylate (10 g, 52.8 mmol) was formylated using POCl3 (1.3 equiv.) and DMF (1.3 equiv.) as above to give 3-formyl-1H-indole-2-carboxylic acid ethyl ester as a white solid.

Sources & evidence

ORD record: ord-1c23ee20681a4d60ab465765200aa4b8
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06855730B2

Reaction notes

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