Hydrochloric Acid → Dimethyl 2-methyl-4-(2-cyanophenyl)-6-formyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 1164638Notes

Reaction equation

HRID 1164638 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH:24](OC)[O:25]C)=[C:5]([C:20]([O:22][CH3:23])=[O:21])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]#[N:19])[C:7]=1[C:8]([O:10][CH3:11])=[O:9].Cl.C(=O)(O)[O-].[Na+]>CC(C)=O.O>[CH3:1][C:2]1[NH:3][C:4]([CH:24]=[O:25])=[C:5]([C:20]([O:22][CH3:23])=[O:21])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]#[N:19])[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 12896947HCID 12896947, compound

Product 1

HCID 15737326Dimethyl 2-methyl-4-(2-cyanophenyl)-6-formyl-1,4-dihydropyridine-3,5-dicarboxylate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

To a solution of dimethyl 2-methyl-4-(2-cyanophenyl)-6-dimethoxymethyl-1,4-dihydropyridine-3,5-dicarboxylate (6.0 ) in acetone (60 mg) was added 6N hydrochloric acid (6 ml), and the resultant mixture was stirred for 3 hours at room temperature. The reaction mixture was diluted with water (30 ml), and adjusted to pH 7.5 with an aqueous sodium bicarbonate solution, and acetone was distilled off under reduced pressure. The resultant crystalline mass was crushed as finely as possible with a glass rod, washed wth an additional water (100 ml), collected by filtration, further washed thoroughly with water, and air-dried to give crystalline powder of dimethyl 2-methyl-4-(2-cyanophenyl)-6-formyl-1,4-dihydropyridine-3,5-dicarboxylate (5.19g).

Workup

  1. distillationwas distilled off under reduced pressure
  2. customThe resultant crystalline mass was crushed as finely as possible with a glass rod
  3. washwashed wth an additional water (100 ml)
  4. filtrationcollected by filtration
  5. washfurther washed thoroughly with water
  6. customair-dried

Sources & evidence

ORD record
ord-7eeeefe61ebd43e08d85f3d9946e76b6
Source dataset
uspto-grants-1983_01
Patent number
US04370334

Reaction notes

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