Acetic Acid → Pipemidic Acid

HRID 1658134Notes

Reaction equation

HRID 1658134 reaction equation
C([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:11]=[CH:12][C:13]3[C:19](=[O:20])[C:18]([C:21]([O:23]CC)=[O:22])=[CH:17][N:16]([CH2:26][CH3:27])[C:14]=3[N:15]=2)[CH2:6][CH2:5]1)(=O)C.C(O)(=O)C>[OH-].[Na+]>[CH2:26]([N:16]1[C:14]2[N:15]=[C:10]([N:7]3[CH2:6][CH2:5][NH:4][CH2:9][CH2:8]3)[N:11]=[CH:12][C:13]=2[C:19](=[O:20])[C:18]([C:21]([OH:23])=[O:22])=[CH:17]1)[CH3:27]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 12917682Ethyl 2-(4-acetyl-1-piperazinyl)-5,8-dihydro-8-ethyl-5-oxopyrido[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 4831Pipemidic AcidYield 84.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Ethyl 2-(4-acetyl-1-piperazinyl)-5,8-dihydro-8-ethyl-5-oxopyrido[2,3 -d]pyrimidine-6-carboxylate (1.6 g) was dissolved in 30 ml of a 10% aqueous solution of sodium hydroxide by heating at 90° - 95°C for one hour. Neutralization of the reaction mixture with acetic acid under cooling yielded a crude solid, which was recrystallized from dimethylformamide to give 1.1 g of the product as a pure state.

Workup

  1. temperatureby heating at 90° - 95°C for one hour
  2. customyielded a crude solid, which
  3. customwas recrystallized from dimethylformamide

Sources & evidence

ORD record
ord-ff5e52a4e0c04f678111252b2eba2890
Source dataset
uspto-grants-1976_06
Patent number
US03962443

Reaction notes

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