Dimethylformamide dimethyl acetal → (2e)-1-(1-Acetyl-2,3-dihydro-1h-indol-5-yl)-3-(dimethylamino)prop-2-en-1-one

HRID 1510239Notes

Reaction equation

HRID 1510239 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](=[O:15])[CH3:14])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].CO[CH:18](OC)[N:19]([CH3:21])[CH3:20]>>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](=[O:15])/[CH:14]=[CH:18]/[N:19]([CH3:21])[CH3:20])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 32808501,5-Diacetylindoline

Product 1

HCID 69081893(2e)-1-(1-Acetyl-2,3-dihydro-1h-indol-5-yl)-3-(dimethylamino)prop-2-en-1-oneYield 97%

Conditions

Temperature
110 °C

Procedure

A mixture of 1-(1-acetyl-2,3-dihydro-1H-indol-5-yl)ethanone (6.0 g) and N,N-dimethylformamide dimethylacetal (14.2 g) was refluxed at 110° C. for 4 hours and evaporated in vacuo. The residue was triturated with diisopropylether, collected by filtration, and dried in vacuo to afford crude (2E)-1-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-3-(dimethylamino)prop-2-en-1-one (7.4 g). To a solution of crude product in methanol (100 mL) were added guanidine hydrochloride (3.56 g) and potassium tert-butoxide (3.86 g) and the mixture was stirred at 100° C. for 3 hours.

Workup

  1. customevaporated in vacuo
  2. customThe residue was triturated with diisopropylether
  3. filtrationcollected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-d8d0e88410084b32bc70e927126b07f1
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

Loading…