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

HRID 1057591

反応式

HRID 1057591 の反応式
[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

参加物

4

反応物 2

HCID 7516PhenylhydrazineHCID 104341,3-Cyclohexanedione

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8c937aac88464cedb42456e301ffaf4d
出典データセット
uspto-grants-2003_02
特許番号
US06514968B1

関連ノート

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