Hydrochloric Acid → 5-Carboxy-2-(2-propoxyphenyl)pyrimidin-4(3H)-one

HRID 437444Notes

Reaction equation

HRID 437444 reaction equation
[O:1]=[C:2]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH2:15][CH2:16][CH3:17])=[N:5][CH:4]=[C:3]1[C:18]([O:20]CC)=[O:19].Cl.C(O)C>[OH-].[Na+]>[O:1]=[C:2]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH2:15][CH2:16][CH3:17])=[N:5][CH:4]=[C:3]1[C:18]([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 12535801Ethyl 1,6-dihydro-6-oxo-2-(2-propoxyphenyl)pyrimidine-5-carboxylate

Product 1

HCID 125358445-Carboxy-2-(2-propoxyphenyl)pyrimidin-4(3H)-oneYield 97.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of ethyl 1,6-dihydro-6-oxo-2-(2-n-propoxyphenyl)pyrimidine-5-carboxylate (3.02 g., 0.01 mole) in 1N sodium hydroxide (22 ml.) was heated on a steam bath for 20 minutes. The cooled solution was treated with 1N hydrochloric acid (23 ml.). The precipitated 1,6-dihydro-6-oxo-2-(2-n-propoxyphenyl)pyrimidine-5-carboxylic acid (2.67 g., 97.4% yield), m.p. 203°-206°, was recrystallized from ethanol to give product with m.p. 205.5°-207.5°.

Sources & evidence

ORD record
ord-b1129ed326ee4bd8975bb5d8a0a8e270
Source dataset
uspto-grants-1977_06
Patent number
US04031093

Reaction notes

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