Dimethylformamide diethylacetal → HCID 54029226, compound

HRID 1077558Notes

Reaction equation

HRID 1077558 reaction equation
[C:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[N:6][CH:5]=1)(=[O:3])[CH3:2].C(O[CH:17](OCC)[N:18]([CH3:20])[CH3:19])C>>[CH3:17][N:18]([CH3:20])[CH:19]=[CH:2][C:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[N:6][CH:5]=1)=[O:3]

Participants

3

Reactant 2

HCID 70913Dimethylformamide diethylacetalHCID 132273241-(Isoquinolin-4-yl)ethan-1-one

Product 1

HCID 54029226HCID 54029226, compound

Procedure

2.0 g (11.6 mmol) of 4-acetylisoquinoline [J. Chem. Soc., Perkin Trans. 1, (7), 1503-8]are stirred in 50 ml of dimethyl formamide diethyl acetal for 1 hour at 110° C. The reaction mixture is concentrated under reduced pressure and the residue is chromatographed (methylene chloride:methanol=95:5), giving 3-dimethylamino-1-(4-isoquinolinyl)-2-propen-1-one; 1H-NMR (dimethyl sulfoxide): 2.9 (3H,s), 3.1 (3H,s), 5.52 (1H,d), 7.7-8.2 (m,5H), 8.6 (1H,s), 9.35 (1H,s).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customthe residue is chromatographed (methylene chloride:methanol=95:5)

Sources & evidence

ORD record
ord-b86bef24a6ab4e8ba6aeeb81eeb3f2cb
Source dataset
uspto-grants-1996_08
Patent number
US05543520

Reaction notes

Loading…