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

HRID 1614291Notes

Reaction equation

HRID 1614291 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3](C(O)=O)[CH2:2]1.S(O)(O)(=O)=O.[CH3:15][N:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[NH2:17].[OH-:24].[Na+]>O.Cl>[CH3:15][N:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[NH:17][C:4]1[CH2:3][CH2:2][NH:1][C:6](=[O:24])[CH:5]=1

Participants

6

Reactant 3

HCID 4498Nipecotic AcidHCID 14798Sodium HydroxideHCID 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 962WaterSolvent3×

Procedure

A mixture of 3-piperidinecarboxylic acid, 2,4-dioxo-, methyl ester (10.0 g) in industrial methylated spirits and water (1:1) (50 ml) and 5M aqueous hydrochloric acid (0.4 ml) was heated at 50°-55° for 30 min, and then heated at reflux for 1.5 h. The resulting mixture was cooled to room temperature and treated with 1-methyl-1-phenylhydrazine sulphate (2:1) (9.9 g) and 5M aqueous sodium hydroxide (11.6 ml). Water (5.5 ml) was added, and more water (33 ml) was added slowly over 45 min. The resultant solid was filtered off, washed with water (3×8 ml) and dried in vacuo at 43° to give the title compound (10.7 g), m.p. 180°-181°.

Workup

  1. temperaturewas heated at 50°-55° for 30 min
  2. temperatureheated
  3. temperatureat reflux for 1.5 h
  4. filtrationThe resultant solid was filtered off
  5. washwashed with water (3×8 ml)
  6. customdried in vacuo at 43°

Sources & evidence

ORD record
ord-0d5bd5d1023e4f87a5de63cb94568458
Source dataset
uspto-grants-1993_03
Patent number
US05196534

Reaction notes

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