Water → HCID 54010553, compound

HRID 275758Notes

Reaction equation

HRID 275758 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[O:11])=[CH:5][CH:4]=1.CO[CH:20](OC)[N:21]([CH3:23])[CH3:22].O>CN(C)C=O>[CH3:20][N:21]([CH3:23])[CH:22]=[C:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[C:10]([C:12]1[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=1)=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 78373Dimethylformamide dimethyl acetalHCID 11009692HCID 11009692, compound

Product 1

HCID 54010553HCID 54010553, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(4-methoxyphenyl)-1-(pyridin-4-yl)ethanone (10.2 g) and dimethylformamide-dimethylacetal (20 cm3) in dry dimethylformamide (50 cm3) was stirred at 80° C. for 4 hours. The mixture was cooled, poured into water (500 cm3) and extracted with ethyl acetate (3×200 cm3). The combined extracts were washed with brine (100 cm3), dried (magnesium sulphate), filtered and concentrated to give a yellow solid. The material was washed well with diethyl ether-hexane (1:9; 2×100 cm3) and dried in vacuo to give 3-dimethylamino-2-(4-methoxyphenyl)-1-(pyridin-4-yl)propen-1-one as a beige solid (7.7 g; 60%). δH (250 MHz; CDCl3) 2.78 [6 H, broad s, N(CH3)2], 3.79 (3 H, s, OCH3), 6.79 (2 H, d, J 9, methoxyphenyl H-2), 7.04 (2 H, d, J 9, methoxyphenyl H-3), 7.24 (2 H, d, J 6, pyridyl H-3) 7.40 (1 H, s, C═CH) and 8.51 (2 H, d, J 6, pyridyl H-2).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate (3×200 cm3)
  3. washThe combined extracts were washed with brine (100 cm3)
  4. dry with materialdried (magnesium sulphate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a yellow solid
  8. washThe material was washed well with diethyl ether-hexane (1:9; 2×100 cm3)
  9. customdried in vacuo

Sources & evidence

ORD record
ord-7068524edaac49f6a21c7f1b4e0927db
Source dataset
uspto-grants-2002_03
Patent number
US06352994B2

Reaction notes

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