Hydrochloric Acid → 2-(4-Chlorophenyl)-6-hydroxypyrimidine-4-carboxylic acid

HRID 2403101

Reaction equation

HRID 2403101 reaction equation
[Na].[C:2]([O:12]CC)(=[O:11])[CH2:3][C:4]([C:6]([O:8]CC)=O)=O.[OH-].[Na+].Cl.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=[NH:27])[NH2:26])=[CH:21][CH:20]=1.Cl>O>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[NH:27][C:6](=[O:8])[CH:4]=[C:3]([C:2]([OH:12])=[O:11])[N:26]=2)=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2034364-Chlorobenzene-1-carboximidamide hydrochlorideHCID 57351814Diethyl 2-oxosuccinate,sodium salt

Product 1

HCID 1358788822-(4-Chlorophenyl)-6-hydroxypyrimidine-4-carboxylic acidYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of diethyl oxalacetate sodium salt (123.2 g, 586 mmol) in water (750 mL) was slowly added aqueous sodium hydroxide (50%, 47 g, 586 mmol). After 1 h the solids had dissolved. 4-Chlorobenzenecarboximidamide monohydrochloride (111.95 g, 586 mmol) was then added, and the mixture was heated at 70° C. overnight. After cooling to room temperature concentrated hydrochloric acid was slowly added (causing foaming) until the pH was lowered to 1.5. The solid was isolated by filtration and washed with water and methanol. The solid was then triturated twice with hot methanol, washed repeatedly with 1 N hydrochloric acid, then once with methanol and dried to afford the title compound (66.07 g).

Workup

  1. dissolutionAfter 1 h the solids had dissolved
  2. additionwas slowly added (causing foaming) until the pH
  3. customThe solid was isolated by filtration
  4. washwashed with water and methanol
  5. customThe solid was then triturated twice with hot methanol
  6. washwashed repeatedly with 1 N hydrochloric acid
  7. dry with materialonce with methanol and dried

Sources & evidence

ORD record
ord-9a17f74b9934431aad3f7af54811b347
Source dataset
uspto-grants-2014_08
Patent number
US08802597B2

Linked notes

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