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Ethanol → 2,6-Dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-[4-(2-tetrahydropyran-2-yloxyethyl)phenoxy]propoxycarbonyl)-1,4-dihydropyridine

HRID 34415
Notes
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Reaction equation

HRID 34415 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:33])=[C:5]([C:21]([O:23][CH2:24][CH2:25][CH2:26]CCCCCBr)=[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].[CH3:34][O:35][C:36](=O)[CH2:37][C:38]1[CH:43]=[CH:42][C:41](SCC2C=CC=CC=2)=[CH:40][CH:39]=1.[N+]([C:56]1[CH:57]=[C:58](C=CC=1)[CH:59]=[O:60])([O-])=O.C([OH:66])C>>[CH3:1][C:2]1[NH:3][C:4]([CH3:33])=[C:5]([C:21]([O:23][CH2:24][CH2:25][CH2:26][O:66][C:41]2[CH:40]=[CH:39][C:38]([CH2:37][CH2:36][O:35][CH:34]3[CH2:56][CH2:57][CH2:58][CH2:59][O:60]3)=[CH:43][CH:42]=2)=[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

5

Reactant 4

HCID 702EthanolHCID 74493-NitrobenzaldehydeHCID 201295212,6-Dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(8-bromooctyloxycarbonyl)-1,4-dihydropyridineHCID 54174016Methyl(4-benzylthiophenyl)acetate

Product 1

HCID 142087862,6-Dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-[4-(2-tetrahydropyran-2-yloxyethyl)phenoxy]propoxycarbonyl)-1,4-dihydropyridine

Procedure

A mixture of 3-(4-[2-(tetrahydropyran-2-yloxy)ethyl]phenoxy)propyl acetoacetate (2, 5 g), methyl 3-aminocrotonate (3, 2.3 g), 3-nitrobenzaldehyde (4, 2.9 g) and ethanol (70 mL) is heated at reflux for about 12 hours. The solvent is removed under reduced pressure and the residue purified using silica gel chromatography (90/10CH2Cl2 /acetone) to yield 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-[3-(4-[2-(tetrahydropyran-2-yloxy)ethyl]phenoxy)propoxycarbonyl]-1,4-dihydropyridine (1, mp<55° C.).

Workup

  1. temperatureis heated
  2. temperatureat reflux for about 12 hours
  3. customThe solvent is removed under reduced pressure
  4. customthe residue purified

Sources & evidence

ORD record
ord-eb9ebf900137450299afcd3bf8520aa1
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