Lithium hydroxide, monohydrate → 5-Cyclopropyl-6-(2,4-dichloro-phenylamino)-pyridine-2-carboxylic acid

HRID 927338ノート

反応式

HRID 927338 の反応式
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:13][CH2:12]2)=[C:7]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[N:6]=1)=[O:4].O.[OH-].[Li+]>C1COCC1.O>[CH:11]1([C:8]2[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][C:7]=2[NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[CH2:12][CH2:13]1

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 710873965-Cyclopropyl-6-(2,4-dichloro-phenylamino)-pyridine-2-carboxylic acid methyl ester

生成物 1

HCID 710872815-Cyclopropyl-6-(2,4-dichloro-phenylamino)-pyridine-2-carboxylic acid収率 10.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 5-cyclopropyl-6-(2,4-dichloro-phenylamino)-pyridine-2-carboxylic acid methyl ester (62 mg, 184 μmol) and lithium hydroxide hydrate (9.3 mg, 221 μmol) in THF (100 μl) and water (50 μl) was stirred at ambient temperature for 20 h. The reaction mixture was poured onto 1 M HCl/ice water (1×20 mL) and extracted with i-PrOAc (2×25 mL). The combined organic layers were dried over sodium sulfate. The solvent was removed under reduced pressure to obtain the title compound (6 mg, 10%) as colorless liquid, which was sufficiently pure to be used in the next reaction step, MS (EI): m/e=323.3 [M+H]+.

後処理

  1. extractionextracted with i-PrOAc (2×25 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-23c1b1f9ebd6476094bd51c7c3cc5c7a
出典データセット
uspto-grants-2016_03
特許番号
US09290451B2

反応ノート

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