1H-Indazol-5-ol → 5-hydroxy-4-(N-phenyliminomethyl)-1H-indazole

HRID 275779

反応式

HRID 275779 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[C:11]1([N:17]=[CH:18]OCC)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)C>[OH:1][C:2]1[C:3]([CH:18]=[N:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2

参加物

4

反応物 2

HCID 1014381H-Indazol-5-olHCID 111236Methanimidic acid, N-phenyl-, ethyl ester

生成物 1

HCID 1355815975-hydroxy-4-(N-phenyliminomethyl)-1H-indazole収率 63.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
175 °C

実験手順

A round bottomed flask containing a mixture of 5-hydroxy-1H-indazole (28.5 g) and ethyl N—phenylformimidate (35 g) was submerged rapidly in an oil bath pre-heated to 175° C. and the mixture stirred at 160-180° C. for 30 minutes, the ethanol produced in the reaction being removed by distillation. The cooled mixture was then treated with boiling methanol (500 ml) and the resultant brown solid collected by filtration, washed with methanol (100 ml) and dried to give 5-hydroxy-4-(N-phenyliminomethyl)-1H-indazole (32 g) as a yellow solid. The solid was dissolved in hydrochloric acid (5 M; 500 ml) and heated at 50-60° C. with stirring for 2 hours. The mixture was diluted with water (500 ml) and extracted with ethyl acetate (2×500 ml). The combined extracts were washed with water (500 ml), dried over magnesium sulphate and the solvent evaporated under reduced pressure to give 5-hydroxy-1H-indazole-4-carboxaldehyde (15.48 g) as a yellow solid.

後処理

  1. additionA round bottomed flask containing
  2. customwas submerged rapidly in an oil bath
  3. custombeing removed by distillation
  4. additionThe cooled mixture was then treated with boiling methanol (500 ml)
  5. filtrationthe resultant brown solid collected by filtration
  6. washwashed with methanol (100 ml)
  7. customdried

出典と根拠

ORDレコード
ord-134e0abbe2a841b8868db4b31880a163
出典データセット
uspto-grants-2002_03
特許番号
US06353002B2

関連ノート

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