Acetic Acid → 1H-Indazole

HRID 1414751노트

반응식

HRID 1414751 반응식
[N:1]([C:4]1[C:9]([CH:10]=O)=[CH:8][C:7](OC)=[C:6](OC)[CH:5]=1)=[N+:2]=[N-].NC1C=CC=CC=1.C(O)(=O)C>CN(C)C=O>[NH:1]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[N:2]1

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 6115AnilineHCID 11344785Benzaldehyde, 2-azido-4,5-dimethoxy-

생성물 1

HCID 92211H-Indazole수율 169.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution containing 51.8 g (0.25 mole) 6-azidoveratraldehyde (Example XII). 26.0 g (0.28 mole) aniline, 4 ml galcial acetic acid, and 300 ml dimethylformamide was stirred at 90°-100° for 1 hr, then refluxed for 1 hr until the gaseous evolution was complete. After the mixture was cooled and poured slowly in 1.5 l. iced water, the product was filtered, washed with two 150 ml portions cold water, and air dried to give 50 g of crude indazole, m.p. 130°-138°. Recrystallization from ethyl acetate--hexane followed by ethyl acetate gave 26 g (41%) of the product, m.p. 149°-152°. Recrystallization from ethyl acetate--hexane gave the analytical sample, m.p. 149°-152°.

후처리

  1. temperaturerefluxed for 1 hr until the gaseous evolution
  2. temperatureAfter the mixture was cooled
  3. additionpoured slowly in 1.5 l
  4. filtrationiced water, the product was filtered
  5. washwashed with two 150 ml portions cold water, and air
  6. customdried

출처 및 근거

ORD 기록
ord-d78d9a25f43f47ad8247b5119df22454
출처 데이터셋
uspto-grants-1977_01
특허 번호
US04002652

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