Hydrochloric Acid → HCID 20043749, compound

HRID 1761881Notes

Reaction equation

HRID 1761881 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH3:19])=[C:9]1[C:20]([O:22][CH3:23])=[O:21].[C:24](Cl)(=[O:26])[CH3:25].Cl>O1CCOCC1.N1C=CC=CC=1>[C:24]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH3:19])=[C:9]1[C:20]([O:22][CH3:23])=[O:21])(=[O:26])[CH3:25]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 30821983,5-Bis(methoxycarbonyl)-2,6,-dimethyl-4-(2-aminophenyl)-1,4-dihydropyridine

Product 1

HCID 20043749HCID 20043749, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 315 mg(1 mmole) of 4-(2-aminophenyl)-2,6-dimethyl-3,5-bis(methoxycarbonyl)-1,4-dihydropyridine [J. Am. Chem. Soc., 71, 4003 (1949)] in 1 ml of dioxane and 1 ml of pyridine a solution of 0.18 g of acetylchloride in 1 ml of dioxane was added drop-wise during 20 minutes in a temperature range of 0° to 10° C., then the mixture was stirred for 40 minutes at this temperature and for 3 hours at room temperature, thereafter it was poured into 10 ml of aqueous 10% hydrochloric acid. The precipitate formed was filtered, washed with water and dried. Yield 350 g (97.5%), m.p. 284° to 285° C. (ethanol).

Workup

  1. customThe precipitate formed
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-bd63d56b68764fd9b7525c67f71c9e16
Source dataset
uspto-grants-1989_05
Patent number
US04829076

Reaction notes

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