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Acetyl chloride → Diethyl 2-methyl-4-(2-nitrophenyl)-6-acetoxymethyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 1248709
Notes
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Reaction equation

HRID 1248709 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH2:27][OH:28])=[C:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[C:29](Cl)(=[O:31])[CH3:30]>N1C=CC=CC=1.C(Cl)Cl>[CH3:1][C:2]1[NH:3][C:4]([CH2:27][O:28][C:29](=[O:31])[CH3:30])=[C:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 133883402-Hydroxymethyl-6-methyl-4-(nitrophenyl)-3,5-diethoxycarbonyl-1,4-dihydropyridine

Product 1

HCID 13388345Diethyl 2-methyl-4-(2-nitrophenyl)-6-acetoxymethyl-1,4-dihydropyridine-3,5-dicarboxylateYield 68.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

To a mixture of diethyl 2-methyl-4-(2-nitrophenyl)-6-hydroxymethyl-1,4-dihydropyridine-3,5-dicarboxylate (2.35 g) in pyridine (30 ml), was dropwise added a solution of acetyl chloride (942 mg) in methylene chloride (5 ml) under stirring and ice-cooling over the period of 7 minutes. The mixture was further stirred for 70 minutes at room temperature. The pyridine was distilled off under reduced pressure and ethyl acetate was added to the residue. The resultant mixture was washed twice with water and adjusted to pH 4 with hydrochloric acid and then an aqueous solution of sodium chloride, dried and concentrated under reduced pressure to give an oily substance. This oily substance was crystallized by treating with a mixture of diethyl ether and a small amount of n-hexane, and collected crude crystals (2.5 g) were washed with n-hexane and thus obtained crystals were recrystallized from diethyl ether to give pure crystals (1.78 g) of diethyl 2-methyl-4-(2-nitrophenyl)-6-acetoxymethyl-1,4-dihydropyridine-3,5-dicarboxylate, m.p. 89° to 90° C.

Workup

  1. temperatureice-cooling over the period of 7 minutes
  2. stirringThe mixture was further stirred for 70 minutes at room temperature
  3. distillationThe pyridine was distilled off under reduced pressure and ethyl acetate
  4. additionwas added to the residue
  5. washThe resultant mixture was washed twice with water
  6. dry with materialan aqueous solution of sodium chloride, dried
  7. concentrationconcentrated under reduced pressure
  8. customto give an oily substance
  9. customThis oily substance was crystallized
  10. additionby treating with a mixture of diethyl ether
  11. customa small amount of n-hexane, and collected crude crystals (2.5 g)
  12. washwere washed with n-hexane and thus obtained crystals
  13. customwere recrystallized from diethyl ether

Sources & evidence

ORD record
ord-a4f5af6ac7ad4f7c909420ad1eb4ac1f
Source dataset
uspto-grants-1985_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04525478

Reaction notes

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