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3-Nitrobenzaldehyde → Nicardipine Impurity 19

HRID 568934
Notes
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Reaction equation

HRID 568934 reaction equation
[C:1]([O-:7])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[N+:8]([C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH:14]=O)([O-:10])=[O:9].C(O)(=O)C.N1CCCCC1.[NH2:29]/[C:30](/[CH3:39])=[CH:31]\[C:32]([O:34][CH2:35][CH2:36][C:37]#[N:38])=[O:33]>C1C=CC=CC=1.C(O)(C)C>[C:37]([CH2:36][CH2:35][O:34][C:32]([C:31]1[CH:14]([C:13]2[CH:16]=[CH:17][CH:18]=[C:11]([N+:8]([O-:10])=[O:9])[CH:12]=2)[C:2]([C:1]([OH:7])=[O:6])=[C:3]([CH3:5])[NH:29][C:30]=1[CH3:39])=[O:33])#[N:38]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 74493-NitrobenzaldehydeHCID 6971017AcetoacetateHCID 9793820Piperidine, acetateHCID 136714102-Cyanoethyl 3-aminocrotonate

Product 1

HCID 10429284Nicardipine Impurity 19Yield 84.1%

Reagents, catalysts & solvents 2

HCID 241
Benzene
Solvent
HCID 3776IsopropanolSolvent

Procedure

20.5 g of 2-nitratopropyl acetoacetate, 15.1 g of 3-nitrobenzaldehyde and 1.5 g of piperidine acetate in 74 ml of benzene were heated at reflux under azeotropic dehydration conditions for 2 hours. The reaction solution was washed, in turn, with 25 ml of water, 25 ml of an aqueous 1N sodium bisulfite solution and 25 ml of water and dried over anhydrous sodium sulfate, and the benzene was evaporated under reduced pressure. To the residue thus obtained was added 15.4 g of 2-cyanoethyl 3-aminocrotonate, and the mixture was taken up in 44 ml of isopropyl alcohol, heated at reflux for 3 hours and cooled on ice. The crystals which precipitated were collected by filtration, dried, applied to a silica gel column chromatography [eluent: a mixture of hexane and ethyl acetate (1:1)] and recrystallized from isopropyl alcohol to give 31.2 g of 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-cyanoethyl) ester 5-(2-nitratopropyl) ester.

Workup

  1. temperatureat reflux under azeotropic dehydration conditions for 2 hours
  2. washThe reaction solution was washed, in turn, with 25 ml of water, 25 ml of an aqueous 1N sodium bisulfite solution and 25 ml of water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe benzene was evaporated under reduced pressure
  5. customTo the residue thus obtained
  6. temperatureheated
  7. temperatureat reflux for 3 hours
  8. temperaturecooled on ice
  9. customThe crystals which precipitated
  10. filtrationwere collected by filtration
  11. customdried
  12. additiona mixture of hexane and ethyl acetate (1:1)] and
  13. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-285af784a44a4ec1b97c1dc94e014538
Source dataset
uspto-grants-1988_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04730052

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes