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

HRID 1057591

Reaction equation

HRID 1057591 reaction equation
[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

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 104341,3-Cyclohexanedione

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8c937aac88464cedb42456e301ffaf4d
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Linked notes

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