Sodium Hydroxide → HCID 19737156, compound

HRID 258232Notes

Reaction equation

HRID 258232 reaction equation
C([O:4][C:5](=[O:25])[C:6]1[CH:11]=[C:10]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([CH3:19])[N:14]([CH3:20])[C:13]2=[O:21])[C:9]([F:22])=[CH:8][C:7]=1[C:23]#[N:24])(C)C.[OH-].[Na+]>CO.O>[C:23]([C:7]1[CH:8]=[C:9]([F:22])[C:10]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([CH3:19])[N:14]([CH3:20])[C:13]2=[O:21])=[CH:11][C:6]=1[C:5]([OH:25])=[O:4])#[N:24]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53787511HCID 53787511, compound

Product 1

HCID 19737156HCID 19737156, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 30.5 g of 2-cyano-5-[3,6-dihydro-3,4-dimethyl-2,6-dioxo-1(2H)-pyrimidinyl]-4-fluorobenzoic acid isopropyl ester (see Example 1) in 150 ml of methanol is maintained at 1°-3° C. for 15 minutes with 4.0 g of sodium hydroxide in 50 ml of water and then stirred for 23 hours. The solution is substantially concentrated by evaporation under reduced pressure and the residue is adjusted to a pH value of 2 with 2N hydrochloric acid. The resulting precipitate is filtered off with suction and subsequently washed with n-hexane to yield 2-cyano-5-[3,6-dihydro-3,4-dimethyl-2,6-dioxo-1(2H)-pyrimidinyl]-4-fluorobenzoic acid, m.p. 232° C. (with decomposition).

Workup

  1. concentrationThe solution is substantially concentrated by evaporation under reduced pressure
  2. filtrationThe resulting precipitate is filtered off with suction
  3. washsubsequently washed with n-hexane

Sources & evidence

ORD record
ord-1dd6c57385a74fa4a3b0d3bb2ae70658
Source dataset
uspto-grants-1993_11
Patent number
US05266554

Reaction notes

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