3-Acetylindole → 3-(dimethylamino)-1-(1H-indol-3-yl)prop-2-en-1-one

HRID 2232293Notes

Reaction equation

HRID 2232293 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)(=[O:3])[CH3:2].C(O[CH:18](N(C)C)[N:19]([CH3:21])[CH3:20])(C)(C)C>>[CH3:18][N:19]([CH3:21])[CH:20]=[CH:2][C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)=[O:3]

Participants

3

Reactant 2

HCID 128023-AcetylindoleHCID 79885tert-Butoxy bis(dimethylamino)methane

Product 1

HCID 14864563-(dimethylamino)-1-(1H-indol-3-yl)prop-2-en-1-one

Procedure

A mixture of 3.18 g of 3-acetylindole and 5.17 ml. (4.36 g) of tert-butoxybis(dimethylamino)methane was heated on a steam bath for 4 hours. The cooled reaction mixture was triturated with n-hexanes and gave a semi-solid. The solvent was removed in vacuo and the material was triturated with dichloromethane giving 3.08 g of the desired compound as a tan crystalline solid, mp 239°-245° C.

Workup

  1. customThe cooled reaction mixture
  2. customwas triturated with n-hexanes
  3. customgave a semi-solid
  4. customThe solvent was removed in vacuo
  5. customthe material was triturated with dichloromethane giving 3.08 g of the desired compound as a tan crystalline solid, mp 239°-245° C.

Sources & evidence

ORD record
ord-078e9aae25324729b660b8f3c2ad97a3
Source dataset
uspto-grants-1988_11
Patent number
US04788195

Reaction notes

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