Sodium Hydroxide → 4-(4-(Pyridin-3-yl)pyrimidin-2-ylamino)benzoic acid

HRID 2232305Notes

Reaction equation

HRID 2232305 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][CH:15]=3)[N:8]=2)[CH:2]=1.[OH-].[Na+]>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:24]=[CH:23][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)[N:8]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 143469694-(4-Pyridin-3-yl-pyrimidin-2-ylamino)-benzoic acid ethyl ester

Product 1

HCID 143469704-(4-(Pyridin-3-yl)pyrimidin-2-ylamino)benzoic acidYield 99.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 19.89 g of 4-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid, ethyl ester in 200 ml of 3A ethanol was added 12.5 ml of 10N sodium hydroxide. This mixture was refluxed on a steam bath for 3 hours and then allowed to evaporate. The residue was taken up in water and treated with 10.4 ml of concentrated hydrochloric acid. The resulting solid was collected and dried, giving 18.11 g of the desired product, mp 311°-317° C.

Workup

  1. temperatureThis mixture was refluxed on a steam bath for 3 hours
  2. customto evaporate
  3. additiontreated with 10.4 ml of concentrated hydrochloric acid
  4. customThe resulting solid was collected
  5. customdried

Sources & evidence

ORD record
ord-2414596ccedd4ab7827ce4f4a7224d7b
Source dataset
uspto-grants-1988_11
Patent number
US04788195

Reaction notes

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