Phenylhydrazine → 1,2,3,9-Tetrahydro-4H-carbazol-4-one

HRID 1057591

반응식

HRID 1057591 반응식
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.[C:9]1([NH:15]N)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O>[CH2:6]1[C:1]2[NH:15][C:9]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:2]=2[C:3](=[O:7])[CH2:4][CH2:5]1

참가 물질

4

반응물 2

HCID 7516PhenylhydrazineHCID 104341,3-Cyclohexanedione

생성물 1

HCID 9291301,2,3,9-Tetrahydro-4H-carbazol-4-one수율 91.5%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

To a solution of 1,3-cyclohexane dione (1.99 g, 17.7 mmol) in water (55 mL) is added phenylhydrazine (1.92 g, 17.7 mmol) in 10 mL of water. A gummy solid quickly formed, which after completion of the addition is scrapped with a spatula to give a solid. The solid is collected, washed with water, and dried in a vacuum oven to give 3.0 g of a tan solid. After drying, the tan solid is stirred at reflux in TFA (25 mL) overnight. Upon cooling, TFA is removed in vacuo and water is added to the residue. The resulting solid is collected, washed with water, and dried to give 1.82 g (55%) of the title compound; mp 218-220° C.; IR (drift) 3150, 3130, 3104, 3093, 3056, 2976, 2954, 2944, 1607, 1577, 1466, 1413, 1251, 1178, 755 cm−1; 1H NMR (CDCl3) δ2.26, 2.64, 3.00, 7.26, 7.35, 8.21, 8.74. Anal. Calcd for C12H11NO: C, 77.81; H, 5.99; N, 7.56. Found: C, 77.82; H, 6.15; N, 7.54.

후처리

  1. customA gummy solid quickly formed
  2. additionwhich after completion of the addition
  3. customto give a solid
  4. customThe solid is collected
  5. washwashed with water
  6. customdried in a vacuum oven

출처 및 근거

ORD 기록
ord-8c937aac88464cedb42456e301ffaf4d
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06514968B1

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