Water → N-(1,3,4,9-tetrahydro-2H-carbazol-2-yl)acetamide

HRID 66782Notes

Reaction equation

HRID 66782 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH:4]([NH:8][C:9](=[O:11])[CH3:10])[CH2:3]1.[C:12]1([NH:18]N)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>CC(O)=O>[CH2:3]1[C:2]2[NH:18][C:12]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:7]=2[CH2:6][CH2:5][CH:4]1[NH:8][C:9](=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 7516PhenylhydrazineHCID 20529251N-(3-oxocyclohexyl)acetamide

Product 1

HCID 20529236N-(1,3,4,9-tetrahydro-2H-carbazol-2-yl)acetamideYield 81%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred solution of 140.9 g (0.909 mol) of N-(3-oxocyclohexyl)acetamide in 900 ml of glacial HOAc was heated at 85°-95° C. while 98.2 g (0.909 mol) of phenylhydrazine was added dropwise during 1 hr. After an additional 3 hr at 95°±5°, the hot solution was poured into 5 l. of H2O. When the initially formed gum had solidified, the product was filtered, washed with 2.5 l. of H2O, then 2 l. of Et2O to give 167.6 g (81%) of a grey solid, mp 203°-206°. Recrystallization was best effected by dissolving the crude solid in boiling Me2CO (1 g/25 ml) and boiling down to 1 g/10 ml. The resulting yellow solid (133.5 g, mp 208°-209°) was recrystallized again from Me2CO to yield 111.8 g of white solid, mp 208°-209°. To remove Me2CO occluded by the crystalline solid, the product was further recrystallized from EtOH, 86% recovery of white solid, mp 208°-209°.

Workup

  1. additionwas added dropwise during 1 hr
  2. additionthe hot solution was poured into 5 l
  3. filtrationthe product was filtered
  4. washwashed with 2.5 l

Sources & evidence

ORD record
ord-df1f6941d76e49ac9c6a2d0473aba239
Source dataset
uspto-grants-1982_08
Patent number
US04343812

Reaction notes

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