Sodium Hydroxide → HCID 10449599, compound

HRID 255721Notes

Reaction equation

HRID 255721 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[C:3]=1[C:23]([O:25]CC)=[O:24].[OH-].[Na+]>C(O)C.O>[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[C:3]=1[C:23]([OH:25])=[O:24]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15147509HCID 15147509, compound

Product 1

HCID 10449599HCID 10449599, compoundYield 39.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of ethyl 6-methyl-2-phenyl-4-(4-nitrophenyl)-5-pyrimidinecarboxylate (39 g) and aqueous sodium hydroxide (5.19 g in 10 ml H2O) in ethanol (390 ml) and water (195 ml) was refluxed for 10 hours. After evaporating the solvent, the residue was dissolved in a suspension of water (200 ml) and chloroform (200 ml) under stirring. The separated aqueous layer was adjusted to pH 3.0 with 10% aqueous HCl. The resulting precipitate was collected by filtration, washed with water and dried in vacuo to give 6-methyl-2-phenyl-4-(4-nitrophenyl)-5-pyrimidinecarboxylic acid (14.3 g).

Workup

  1. temperaturewas refluxed for 10 hours
  2. customAfter evaporating the solvent
  3. dissolutionthe residue was dissolved in a suspension of water (200 ml) and chloroform (200 ml)
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-d8d6f76947a04128ac825376ce992d6e
Source dataset
uspto-grants-1987_10
Patent number
US04698340

Reaction notes

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