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3-Bromo-1-propanol → 3-bromopropyl Methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

HRID 34413
Notes
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Reaction equation

HRID 34413 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:24])=[C:5]([C:21](O)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].S(Cl)(Cl)=O.[Br:29][CH2:30][CH2:31][CH2:32][OH:33]>C(Cl)Cl.CN(C=O)C>[CH3:1][C:2]1[NH:3][C:4]([CH3:24])=[C:5]([C:21]([O:33][CH2:32][CH2:31][CH2:30][Br:29])=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 123083-Bromo-1-propanolHCID 24386Thionyl ChlorideHCID 1733222,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester

Product 1

HCID 32742783-bromopropyl Methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-carboxy-1,4-dihydropyridine (107 g, 0.32 mol) in CH2Cl2 (520 mL) and DMF (100 mL) was cooled to 0° C. and thionyl chloride (28 mL, 0.39 mol) slowly added. The mixture was stirred at room temperature for 1 hour, then cooled to 5° C. Distilled 3-bromopropanol (35 mL, 3.9 mol) was slowly added, and the solution stirred for 1 hour at room temperature. The solution was then washed with water and the organic layer dried over sodium sulfate and evaporated under reduced pressure. The product was recrystallized from ethyl acetate to yield 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-bromopropoxycarbonyl)-1,4-dihydropyridine (12, mp=146° C.).

Workup

  1. temperaturecooled to 5° C
  2. stirringthe solution stirred for 1 hour at room temperature
  3. washThe solution was then washed with water
  4. dry with materialthe organic layer dried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-456b9033347340a1acbd3539a4ba158d
Source dataset
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04761420

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes