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

HRID 2403101

反応式

HRID 2403101 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9a17f74b9934431aad3f7af54811b347
出典データセット
uspto-grants-2014_08
特許番号
US08802597B2

関連ノート

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