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Ammonium Hydroxide → 1,4,5,6,7,8-Hexahydro-2-methyl-5-oxo-7-phenylmethyl-4-[2-(trifluoromethyl)phenyl]-1,7-naphthyridine-3-carboxylic acid, 2-(N-benzyl-N-methylamino)ethyl ester

HRID 2059090
Notes
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Reaction equation

HRID 2059090 reaction equation
[CH2:1]([N:8]1[CH2:13][C:12](O)=[CH:11][C:10](=[O:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:16][C:17]([F:27])([F:26])[C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH:20]=O.[C:28]([O:34][CH2:35][CH2:36][N:37]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH3:38])(=[O:33])[CH2:29][C:30]([CH3:32])=O.[OH-].[NH4+:47]>C(O)(C)C>[CH3:32][C:30]1[NH:47][C:12]2[CH2:13][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9][C:10](=[O:15])[C:11]=2[CH:20]([C:19]2[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=2[C:17]([F:27])([F:26])[F:16])[C:29]=1[C:28]([O:34][CH2:35][CH2:36][N:37]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH3:38])=[O:33]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 123067o-(Trifluoromethyl)benzaldehydeHCID 117768292-(Benzylmethylamino)ethyl acetoacetateHCID 129006921-Benzyl-5-hydroxy-1,6-dihydropyridin-3(2H)-one

Product 1

HCID 128184751,4,5,6,7,8-Hexahydro-2-methyl-5-oxo-7-phenylmethyl-4-[2-(trifluoromethyl)phenyl]-1,7-naphthyridine-3-carboxylic acid, 2-(N-benzyl-N-methylamino)ethyl ester

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 15.2 g. of 1-benzyl-3-oxo-5-hydroxy-1,2,3,6-tetrahydropyridine, 13.1 g. of o-trifluoromethylbenzaldehyde, 18.7 g. of 2-(N-benzyl-N-methylamino)ethyl acetoacetate, 6 ml. of 28% ammonium hydroxide and 200 ml. of isopropanol was heated at reflux for 3 hours. The solution was evaporated to dryness. The residue was dissolved in 100 ml. of methylenechloride and extracted with 150 ml. of 15% hydrochloric acid. The acid extract was cooled and made basic with saturated sodium carbonate solution. The mixture was extracted with methylenechloride. The methylenechloride solution was dried over magnesium sulfate, then evaporated in vacuo to a solid residue. The residue was recrystallized from ethanol to obtain the title compound, m.p. 183°-185° C.

Workup

  1. additionA mixture of 15.2 g
  2. temperatureat reflux for 3 hours
  3. customThe solution was evaporated to dryness
  4. dissolutionThe residue was dissolved in 100 ml
  5. extractionof methylenechloride and extracted with 150 ml
  6. extractionThe acid extract
  7. temperaturewas cooled
  8. extractionThe mixture was extracted with methylenechloride
  9. dry with materialThe methylenechloride solution was dried over magnesium sulfate
  10. customevaporated in vacuo to a solid residue
  11. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-7165624d800142b3b136e0fa8e6bdd51
Source dataset
uspto-grants-1982_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04321384

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes