Ethyl formate → 1,5,6,7-Tetrahydro-5-(hydroxymethylene)-1-methyl-4h-indazol-4-one

HRID 569907

반응식

HRID 569907 반응식
[CH3:1][N:2]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[O:11])[C:5]=2[CH:4]=[N:3]1.[H-].[Na+].[CH:14](OCC)=[O:15]>C(O)C.C1(C)C=CC=CC=1>[OH:15][CH:14]=[C:7]1[CH2:8][CH2:9][C:10]2[N:2]([CH3:1])[N:3]=[CH:4][C:5]=2[C:6]1=[O:11]

참가 물질

6

반응물 3

HCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 27657961-Methyl-1,5,6,7-tetrahydro-4H-indazol-4-one

생성물 1

HCID 571627141,5,6,7-Tetrahydro-5-(hydroxymethylene)-1-methyl-4h-indazol-4-one

시약·촉매·용매 2

HCID 702Ethanol촉매HCID 1140Toluene용매

실험 절차

A stirred mixture 16.8 grams of 1,5,6,7-tetrahydro-1-methyl-4H-indazol-4-one, 6 grams of 97% sodium hydride, 15 ml of ethyl formate, 3 drops of ethanol and 200 ml of toluene was heated at reflux for 16 hours. The mixture was then cooled and extracted twice with water and the aqueous extracts were combined and washed with ethyl ether. The aqueous solution was acidified with 5 N hydrochloric acid to a pH of approximately 4 and the resultant slurry was extracted several times with dichloromethane. The combined dichloromethane extracts were dried over magnesium sulfate and concentrated under reduced pressure to leave a residual dark oil. The oil was triturated with a 50:50 mixture of hexane and ethyl ether to give 1,5,6,7-tetrahydro-5-hydroxymethylene-1-methyl-4H-indazol-4-one melting at about 93°-95° C.

후처리

  1. temperatureat reflux for 16 hours
  2. temperatureThe mixture was then cooled
  3. extractionextracted twice with water
  4. washwashed with ethyl ether
  5. extractionthe resultant slurry was extracted several times with dichloromethane
  6. dry with materialThe combined dichloromethane extracts were dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto leave a residual dark oil
  9. customThe oil was triturated with a 50:50 mixture of hexane and ethyl ether

출처 및 근거

ORD 기록
ord-7c61805d19484f8f8d96b5d159bb9db1
출처 데이터셋
uspto-grants-1988_03
특허 번호
US04734430

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