Hydrochloric Acid → HCID 15737330, compound

HRID 894727Notes

Reaction equation

HRID 894727 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-3401b991a9da4d16b79ad8857fb61222
Source dataset
uspto-grants-1981_08
Patent number
US04284634

Reaction notes

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