Water → HCID 13389004, compound

HRID 255498Notes

Reaction equation

HRID 255498 reaction equation
C([O:3][C:4]([C:6]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[C:10]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:9]([CH3:24])[NH:8][C:7]=1[CH:25]=[CH:26][N:27](C)C)=O)C.O>N.C(O)C>[CH2:22]([O:21][C:19]([C:10]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[C:6]2[C:4](=[O:3])[NH:27][CH:26]=[CH:25][C:7]=2[NH:8][C:9]=1[CH3:24])=[O:20])[CH3:23]

Participants

5

Reactant 2

HCID 962WaterHCID 88668155HCID 88668155, compound

Product 1

HCID 13389004HCID 13389004, compound

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 702EthanolSolvent

Procedure

6.0 g (14.3 mmol) 1,4-dihydro-4-(3-chlorophenyl)-2-(2-dimethylamino ethenyl)-6-methyl pyridine-3,5-dicarboxylic acid diethyl ester are kept for six hours at boiling temperature in a mixture of 60 ml concentrated aqueous ammonia solution and 60 ml ethanol. After cooling, the solution is reduced to half the volume under vacuum. Water is added and the solution is extracted twice with chloroform. The chloroform solution is washed with a small amount of water and dried over sodium sulfate. The residue obtained after distilling off the solvent is chromatographed over silica gel with methylene chloride/methanol.ammonia (9:1, v/v) and recrystallized from methanol. There is obtained 1,4,5,6-tetrahydro-4-(3-chlorophenyl)-2-methyl-5-oxo-1,6-naphthyridine-3-carboxylic acid ethyl ester in form of beige crystals with a melting point of 152°-155° C. (decomposition).

Workup

  1. temperatureAfter cooling
  2. extractionthe solution is extracted twice with chloroform
  3. washThe chloroform solution is washed with a small amount of water
  4. dry with materialdried over sodium sulfate
  5. customThe residue obtained
  6. distillationafter distilling off the solvent
  7. customis chromatographed over silica gel with methylene chloride/methanol
  8. customammonia (9:1, v/v) and recrystallized from methanol

Sources & evidence

ORD record
ord-b5f596f0225c4f2881995d3031f039ff
Source dataset
uspto-grants-1987_10
Patent number
US04698341

Reaction notes

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