Acetic Acid → 1H-Indazole

HRID 597499ノート

反応式

HRID 597499 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 92211H-Indazole収率 169.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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 1. 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° .

後処理

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

出典と根拠

ORDレコード
ord-3a273590390d4abbb975c7648b418a52
出典データセット
uspto-grants-1977_03
特許番号
US04014878

反応ノート

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