Hydrochloric Acid → HCID 15665156, compound

HRID 614601Notes

Reaction equation

HRID 614601 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH:36](OCC)[O:37]CC)=[C:5]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:6]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=2)[C:7]=1[C:8]([O:10][CH2:11][CH2:12][N:13]([CH3:21])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:9].Cl>CC(C)=O>[CH3:1][C:2]1[NH:3][C:4]([CH:36]=[O:37])=[C:5]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:6]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=2)[C:7]=1[C:8]([O:10][CH2:11][CH2:12][N:13]([CH3:21])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15665121HCID 15665121, compound

Product 1

HCID 15665156HCID 15665156, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-(N-methyl-N-benzylamino)-ethyl 2-methyl-4-(3-nitrophenyl)-5-ethoxycarbonyl-6-diethoxymethyl-1,4-dihydropyridine-3-carboxylate (7.25 g) in acetone (70 ml) was added 6N-hydrochloric acid (7 ml) and the resultant mixture was stirred at room temperature for 3 hours. The solvent was distilled off under reduced pressure. Water was added to the residue, where an oily substance appeared. The aqueous mixture was adjusted to an alkaline medium by addition of power of sodium bicarbonate, and then extracted with ethyl acetate. The extract was washed with water and dried, and the solvent was distilled off under reduced pressure to give a reddish oil (5.8 g) of 2-(N-methyl-N-benzylamino)-ethyl 2-methyl-4-(3-nitrophenyl)-5-ethoxycarbonyl-6-formyl-1,4-dihydropyridine-3-carboxylate.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionWater was added to the residue, where an oily substance
  3. additionThe aqueous mixture was adjusted to an alkaline medium by addition of power of sodium bicarbonate
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-68f45d6a93d14e2eb3193adc8a8210bc
Source dataset
uspto-grants-1979_03
Patent number
US04145432

Reaction notes

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