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

HRID 614618
Notes
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Reaction equation

HRID 614618 reaction equation
C1C=CC=CC=1.[CH3:7][C:8]1[NH:9][C:10]([CH2:33][OH:34])=[C:11]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N+:25]([O-:27])=[O:26])[C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[C:35](Cl)(=[O:37])[CH3:36]>N1C=CC=CC=1.C(Cl)Cl>[CH3:7][C:8]1[NH:9][C:10]([CH2:33][O:34][C:35](=[O:37])[CH3:36])=[C:11]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N+:25]([O-:27])=[O:26])[C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 241BenzeneHCID 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 1049
Pyridine
Solvent
HCID 6344DichloromethaneSolvent

Procedure

((5) 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 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 amaunt 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 amaunt 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-23e09eb7a49a4c058e4dfb4d6121dd9b
Source dataset
uspto-grants-1979_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04145432

Reaction notes

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