o-(Trifluoromethyl)benzaldehyde → 1,4,5,6,7,8-Hexahydro-2-methyl-5-oxo-7-(phenylmethyl)-4-[2-(trifluoromethyl)phenyl]-1,7-naphthyridine-3-carboxylic acid methyl ester

HRID 2059088Notes

Reaction equation

HRID 2059088 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.[CH3:16][O:17][C:18](=[O:23])/[CH:19]=[C:20](\[NH2:22])/[CH3:21].[F:24][C:25]([F:35])([F:34])[C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH:28]=O>C(O)C>[CH3:16][O:17][C:18]([C:19]1[CH:28]([C:27]2[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=2[C:25]([F:24])([F:34])[F:35])[C:11]2[C:10](=[O:15])[CH2:9][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:13][C:12]=2[NH:22][C:20]=1[CH3:21])=[O:23]

Participants

5

Reactant 3

HCID 123067o-(Trifluoromethyl)benzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 129006921-Benzyl-5-hydroxy-1,6-dihydropyridin-3(2H)-one

Product 1

HCID 128184561,4,5,6,7,8-Hexahydro-2-methyl-5-oxo-7-(phenylmethyl)-4-[2-(trifluoromethyl)phenyl]-1,7-naphthyridine-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 8.5 g. of 1-benzyl-3-oxo-5-hydroxy-1,2,3,6-tetrahydropyridine, 4.75 g. of methyl-3-aminocrotonate (97%), 6.96 g. of o-trifluoromethylbenzaldehyde and 125 ml. of ethanol was refluxed for 2 hours. The mixture was filtered while hot and the filtrate was allowed to cool to room temperature. The solid was separated by filtration. Recrystallization from ethanol afforded the title compound, m.p. 225°-227° C.

Workup

  1. additionA mixture of 8.5 g
  2. filtrationThe mixture was filtered while hot and the filtrate
  3. customThe solid was separated by filtration
  4. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-4215ce00b30f4b349d48016b7d4e008c
Source dataset
uspto-grants-1982_03
Patent number
US04321384

Reaction notes

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