Dimethylformamide dimethyl acetal → 1-Indol-3-yl-2-cyano-3-dimethylaminopropen-1-one

HRID 1370081Notes

Reaction equation

HRID 1370081 reaction equation
[C:1]([CH2:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)=[O:5])#[N:2].CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>>[NH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]([C:4](=[O:5])[C:3]([C:1]#[N:2])=[CH:17][N:18]([CH3:19])[CH3:20])=[CH:7]1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 24535683-(Cyanoacetyl)indole

Product 1

HCID 540937441-Indol-3-yl-2-cyano-3-dimethylaminopropen-1-one

Procedure

1-indol-3-yl-2-cyano-3-dimethylaminopropen-1-one was prepared from 3-(cyanoacetyl) indole (4.0 g, mmol) and dimethylformamide dimethylacetal (4.1 mL, 23.9 mmol) as a yellow solid (2.4 g), m.p. 187-188°. δH (d6 DMSO) 11.73 (1H, bs), 8.26 (1H, s), 8.12 (1H, dd, J 6.8, 1.3 Hz), 7.98 (1H, s), 7.47-7.44 (1H, m), 7.20-7.09 (2H, m), 3.35 (3H, s) and 3.26 (3H, s).

Sources & evidence

ORD record
ord-a24430110edc41c684ff45d6c8d53bd6
Source dataset
uspto-grants-2003_06
Patent number
US06579983B1

Reaction notes

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