Hydrochloric Acid → Oxarbazole

HRID 1605083Notes

Reaction equation

HRID 1605083 reaction equation
[C:1]([N:9]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)N=CC1C=CC=CC=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26]1[CH:32]([C:33]([OH:35])=[O:34])[CH2:31][CH2:30][C:28](=O)[CH2:27]1.Cl>C(O)(=O)C>[C:1]([N:9]1[C:28]2[CH2:27][CH2:26][CH:32]([C:33]([OH:35])=[O:34])[CH2:31][C:30]=2[C:19]2[C:18]1=[CH:23][CH:22]=[C:21]([O:24][CH3:25])[CH:20]=2)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 1927304-Oxocyclohexanecarboxylic acidHCID 68140067HCID 68140067, compound

Product 1

HCID 37184Oxarbazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 75 g. of benzaldehyde 1-benzoyl-1-(4-methoxyphenyl)hydrazone and 42.6 g. of cyclohexanone-4-carboxylic acid in one liter of acetic acid saturated with hydrogen chloride was heated under reflux for three hours during which time hydrogen chloride was continually passed through the solution. The solution was poured into four liters of ice-water and the resulting solid was collected by filtration to give 47.4 g. of the title compound; m.p. 218°-220°C. (methyl alcohol).

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. customto give 47.4 g

Sources & evidence

ORD record
ord-22bc0c41f597461ba535cfadd2d6fe4f
Source dataset
uspto-grants-1976_04
Patent number
US03948939

Reaction notes

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