Ethanol → 1,4,5,6,7,8-Hexahydro-2-methyl-4-(2-methylphenyl)-5-oxo-7-(phenylmethyl)-1,7-naphthyridine-3-carboxylic acid methyl ester

HRID 2059087Notes

Reaction equation

HRID 2059087 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].[C:24]1([CH3:32])[C:25]([CH:30]=O)=[CH:26][CH:27]=[CH:28][CH:29]=1.C(O)C>C(O)(=O)C>[CH3:16][O:17][C:18]([C:19]1[CH:32]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[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

6

Reactant 4

HCID 702EthanolHCID 107222-MethylbenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 129006921-Benzyl-5-hydroxy-1,6-dihydropyridin-3(2H)-one

Product 1

HCID 128184551,4,5,6,7,8-Hexahydro-2-methyl-4-(2-methylphenyl)-5-oxo-7-(phenylmethyl)-1,7-naphthyridine-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 6.1 g. of 1-benzyl-3-oxo-5-hydroxy-1,2,3,6-tetrahydropyridine, 3.6 g. of methyl-3-aminocrotonate (97%), 3.6 g. of o-tolualdehyde, 55 ml. of ethanol and 18 ml. of acetic acid was refluxed for 7 hours. The solution was evaporated to dryness in vacuo. The residue was triturated with diethyl ether and the solid was separated by filtration. Recrystallization from ethanol afforded the title compound, m.p. 201°-204° C.

Workup

  1. additionA mixture of 6.1 g
  2. customThe solution was evaporated to dryness in vacuo
  3. customThe residue was triturated with diethyl ether
  4. customthe solid was separated by filtration
  5. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-54200fc560884c8bb698f0b19a1e03a8
Source dataset
uspto-grants-1982_03
Patent number
US04321384

Reaction notes

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