HCID 13669741, compound → HCID 13669772, compound

HRID 1982577Notes

Reaction equation

HRID 1982577 reaction equation
Cl.[CH3:2][O:3][CH:4]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:5][O:6][C:7]([C:9]1[CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[C:17]2[C:16](=[O:26])[CH2:15][N:14](CC3C=CC=CC=3)[CH2:13][C:12]=2[NH:11][C:10]=1[CH3:34])=[O:8].[H][H]>[Pd].CO>[CH3:2][O:3][CH:4]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:5][O:6][C:7]([C:9]1[CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[C:17]2[C:16](=[O:26])[CH2:15][NH:14][CH2:13][C:12]=2[NH:11][C:10]=1[CH3:34])=[O:8]

Participants

5

Reactant 2

HCID 13669741HCID 13669741, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13669772HCID 13669772, compoundYield 35.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 15.3 g of 1-benzyl-3-hydroxy-5-oxo-2,3,4,6-tetrahydropyridine hydrate, 10.6 g of 3-chlorobenzaldehyde, 17.7 g of 2-methoxy-2-phenylethyl acetoacetate, 12 g of ammonium acetate and 150 ml of methanol was refluxed for 5 huors. The solvent was removed in vacuo. The residue was dissolved in methylenechloride, extracted with water, then dried over magnesium sulfate. The solution was diluted with diethyl ether to the point of cloudiness, then left at room temperature for 18 hours. The supernatant was decanted and the precipitate was slurried with ethanol and filtered to obtain 12.9 g of the solid, mp. 168°-170° C. dec. The solid was suspended in methanol and saturated with hydrogen chloride. The mixture was cooled in an ice bath, then filtered. The solid was recrystallized from ethanol to obtain 11.1 g of 4-(3-chlorophenyl)-1,4,5,6,7,8-hexahydro-2-methyl-5-oxo-7-(phenylmethyl)-1,7-naphthyridine-3-carboxylic acid 2-methoxy-2-phenylethyl ester hydrochloride, mp. 222°-4° C. dec. The hydrochloride (10.8 g), 1 g of 10% palladium on carbon and 450 ml of methanol were shaken with hydrogen at an initial pressure of 48.5 psig. After 4 hours, the catalyst was separated and the solution was evaporated to dryness The residue was dissolved in methanol, saturated with hydrogen chloride, then evaporated to dryness. The residue was recrystallized from ethanol to obtain 3 g of the title compound as the hydrochloride, monohydrate, mp. 165°-7° C.

Workup

  1. customthe catalyst was separated
  2. customthe solution was evaporated to dryness The residue
  3. dissolutionwas dissolved in methanol, saturated with hydrogen chloride
  4. customevaporated to dryness
  5. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-9fed75ece77c421fa9397de227d50750
Source dataset
uspto-grants-1986_06
Patent number
US04596873

Reaction notes

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