1,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamine → Diethyl 5-[3-(dimethylamino)acryloyl]1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate

HRID 54179Notes

Reaction equation

HRID 54179 reaction equation
[C:1]([C:4]1[C:9](=[O:10])[NH:8][C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:5]=1)(=[O:3])[CH3:2].C(O[CH:27](OCC(C)(C)C)[N:28]([CH3:30])[CH3:29])C(C)(C)C>>[CH3:27][N:28]([CH3:30])[CH:29]=[CH:2][C:1]([C:4]1[C:9](=[O:10])[NH:8][C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:5]=1)=[O:3]

Participants

3

Reactant 2

HCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 13752508Diethyl 5-acetyl-1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate

Product 1

HCID 53835628Diethyl 5-[3-(dimethylamino)acryloyl]1,6-dihydro-6-oxo-2,3-pyridinedicarboxylateYield 70%

Procedure

Diethyl 5-acetyl-1,6-dihydro-6-oxo-2,3pyridinedicarboxylate, (25 g, 0.089 mol) and N,N-dimethylformamide dineopentyl acetal (50 mL, 98%, 40.62 g, 0.176 mol) are heated for 30 minutes at 80°-100° C. After cooling to room temperature, the product is obtained as a precipitate and is filtered and washed with hexane to yield 23.4 g, 70% yield, of solid which is recrystallized from isopropanol to give a pure product, melting point 182°-183° C.

Workup

  1. customthe product is obtained as a precipitate
  2. filtrationis filtered
  3. washwashed with hexane
  4. customto yield 23.4 g, 70% yield
  5. customof solid which is recrystallized from isopropanol
  6. customto give a pure product, melting point 182°-183° C.

Sources & evidence

ORD record
ord-b907ec481a21444682d424081944e47e
Source dataset
uspto-grants-1997_04
Patent number
US05622913

Reaction notes

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