Nipecotic Acid → 4-(2-Methyl-2-phenylhydrazinyl)-5,6-dihydropyridin-2(1H)-one

HRID 1614290Notes

Reaction equation

HRID 1614290 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3](C(O)=O)[CH2:2]1.[Na].S(O)(O)(=O)=O.[CH3:16][N:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH2:18].[OH-:25].[Na+]>O.Cl>[CH3:16][N:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH:18][C:4]1[CH2:3][CH2:2][NH:1][C:6](=[O:25])[CH:5]=1

Participants

7

Reactant 4

HCID 4498Nipecotic AcidHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 438107261-Methyl-1-phenylhydrazine sulfate

Product 1

HCID 108569264-(2-Methyl-2-phenylhydrazinyl)-5,6-dihydropyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

A suspension of 3-piperidinecarboxylic acid, 2,4-dioxo-, methyl ester, ion (1-), sodium (10.0 g) in water (24 ml) and 2M aqueous hydrochloric acid (26 ml) was heated at reflux for 30 min. The resulting mixture was cooled to ca. 20°, diluted with industrial methylated spirit (25 ml) and treated with 1-methyl-1-phenylhydrazine sulphate (2:1) (8.8 g) and 5M aqueous sodium hydroxide (12 ml). The resulting suspension was diluted with water (25 ml), cooled to ca. 0° and filtered to give the title compound (9.1 g), m.p. 185°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 min
  3. temperatureThe resulting mixture was cooled to ca. 20°
  4. temperaturecooled to ca. 0°
  5. filtrationfiltered

Sources & evidence

ORD record
ord-caf1d0761eb24742926e8cfe5bd33086
Source dataset
uspto-grants-1993_03
Patent number
US05196534

Reaction notes

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