Acetic Acid → HCID 21452699, compound

HRID 436505Notes

Reaction equation

HRID 436505 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)N)=[CH:4][CH:3]=1.[C:18]([OH:21])(=[O:20])[CH3:19]>C1CCCCC1>[C:10]([N:8]1[C:3]2[CH2:4][CH:19]([C:18]([OH:21])=[O:20])[CH2:6][CH2:7][C:2]=2[C:6]2[C:5]1=[CH:4][CH:3]=[C:2]([Cl:1])[CH:7]=2)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 54089464HCID 54089464, compound

Product 1

HCID 21452699HCID 21452699, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

A stirred mixture of 2.0 g. of N1 -p-chlorophenyl-N1 -benzoylhydrazine, 1.1 g. of cyclohexanone-3-carboxylic acid, 5 ml. of glacial acetic acid and 7 ml. of cyclohexane were heated under an atmosphere of nitrogen. After 3 hours of stirring at reflux, the reaction mixture was concentrated under reduced pressure and 10 ml. of ethanol was added to the residue. After standing overnight in the refrigerator, the insoluble portion was removed by filtration, washed with a small amount of cold ethanol and dried, yielding 0.4 g. of product, m.p. 196°-197° . Following a recrystallization from ethanol, 0.2 g. of 9-benzoyl-6-chloro-1,2,3,4-tetrahydrocarbazole-2-carboxylic acid was obtained, m.p. 207°-208°.

Workup

  1. additionA stirred mixture of 2.0 g
  2. temperatureat reflux
  3. concentrationthe reaction mixture was concentrated under reduced pressure and 10 ml
  4. additionof ethanol was added to the residue
  5. waitAfter standing overnight in the refrigerator
  6. customthe insoluble portion was removed by filtration
  7. washwashed with a small amount of cold ethanol
  8. customdried
  9. customyielding 0.4 g
  10. customa recrystallization from ethanol, 0.2 g

Sources & evidence

ORD record
ord-bf21a542862e41bf9c4c76af71e6088a
Source dataset
uspto-grants-1977_02
Patent number
US04009181

Reaction notes

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