Hydrochloric Acid → HCID 15737330, compound

HRID 1759120Notes

Reaction equation

HRID 1759120 reaction equation
C[O:2][CH:3](OC)[C:4]1[NH:9][C:8]([CH3:10])=[C:7]([C:11]([O:13][CH2:14][CH2:15][CH3:16])=[O:12])[CH:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]#[N:24])[C:5]=1[C:25]([O:27][CH3:28])=[O:26].Cl.C(=O)(O)[O-].[Na+]>CC(C)=O>[CH:3]([C:4]1[NH:9][C:8]([CH3:10])=[C:7]([C:11]([O:13][CH2:14][CH2:15][CH3:16])=[O:12])[CH:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]#[N:24])[C:5]=1[C:25]([O:27][CH3:28])=[O:26])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 15737322HCID 15737322, compound

Product 1

HCID 15737330HCID 15737330, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution (132 ml) of n-propyl 6-dimethoxymethyl-2-methyl-4-(2-cyanophenyl)-5-methoxycarbonyl-1,4-dihydropyridine-3-carboxylate (13.28 g) in acetone was added dropwise 6 N hydrochloric acid (13.2 ml) at 12° C. with stirring, and the stirring was continued for 5.5 hours. The resultant mixture was adjusted to about pH 7 with an aqueous sodium bicarbonate solution. The acetone was distilled off under reduced pressure. The precipitated crystals were collected by filtration and washed with an aqueous sodium chloride solution, water and petroleum ether, successively, and then recrystallized from a mixture of benzene and n-hexane. The crystals were collected by filtration and washed with diethyl ether to give n-propyl 6-formyl-2-methyl-4-(2-cyanophenyl)-5-methoxycarbonyl-1,4-dihydropyridine-3-carboxylate (3.37 g), mp 137.5°-141.0° C.

Workup

  1. distillationThe acetone was distilled off under reduced pressure
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed with an aqueous sodium chloride solution, water and petroleum ether
  4. customsuccessively, and then recrystallized from a mixture of benzene and n-hexane
  5. filtrationThe crystals were collected by filtration
  6. washwashed with diethyl ether

Sources & evidence

ORD record
ord-ac60ef95f3b34fd094bc986edf525b5e
Source dataset
uspto-grants-1982_07
Patent number
US04338322

Reaction notes

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