Sodium Hydroxide → 8-Dimethylamino-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]azulene-5-carboxylic acid amide

HRID 25342

반응식

HRID 25342 반응식
[CH3:1][N:2]([CH3:18])[CH:3]1[C:12]2[CH2:11][O:10][C:9]([C:13]#[N:14])=[CH:8][C:7]3=[CH:15][NH:16][CH:17]=[C:5]([C:6]=23)[CH2:4]1.[OH-:19].[Na+]>>[CH3:1][N:2]([CH3:18])[CH:3]1[C:12]2[CH2:11][O:10][C:9]([C:13]([NH2:14])=[O:19])=[CH:8][C:7]3=[CH:15][NH:16][CH:17]=[C:5]([C:6]=23)[CH2:4]1

참가 물질

3

반응물 2

HCID 14798Sodium HydroxideHCID 697371988-Dimethylamino-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]-azulene-5-carbonitrile

생성물 1

HCID 697364658-Dimethylamino-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]azulene-5-carboxylic acid amide수율 62%

반응 조건

온도
90 °C

실험 절차

Polyphophoric acid 420 mg was added to compound (48) 31.6 mg under an argon atmosphere and the mixture was heated at 90° C. for 6 h. Ice-water was added to the reaction mixture, which was made alkaline with an aqueous 5 N-sodium hydroxide solution and extracted with chloroform. The extracts were washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was chromatographed on aluminum oxide in chloroform:methanol (97:3) to give the titled compound as colorless crystals, 20.9 mg. Yield 62%. Furthermore, the titled compound was recrystallized from acetone-isopropyl ether to give colorless crystals, m.p. 182-183° C.

후처리

  1. extractionextracted with chloroform
  2. washThe extracts were washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. customwas chromatographed on aluminum oxide in chloroform:methanol (97:3)

출처 및 근거

ORD 기록
ord-f83712f482374db8bbb5f7143921623f
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858640B2

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