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

HRID 1532053

반응식

HRID 1532053 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
175 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-96681f8880224ff0b3375d5256c0f7b5
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06201004B1

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