Phenylhydrazine → 1,3-Cyclohexanedione, 1-(2-phenylhydrazone)

HRID 1680378Notes

Reaction equation

HRID 1680378 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.[C:9]1([NH:15][NH2:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[C:9]1([NH:15][N:16]=[C:1]2[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 7516PhenylhydrazineHCID 104341,3-Cyclohexanedione

Product 1

HCID 28029031,3-Cyclohexanedione, 1-(2-phenylhydrazone)

Procedure

Cyclohexane-1,3-dione is reacted with phenylhydrazine to give cyclohexane-1,3-dione monophenylhydrazone which is converted by a Fischer rearrangement into 1,2,3,4-tetrahydro-4-oxo-carbazole (see Annalen, 278, 39/1894; J.C.S., 1951, 700), dehydration of which gives 4-hydroxycarbazole. Of decisive importance for the economic carrying out of this process is the discovery of a suitable method of dehydration or of a suitable dehydration catalyst.

Sources & evidence

ORD record
ord-0d8101b5021048d2b33c0e1222070b46
Source dataset
uspto-grants-1981_06
Patent number
US04273711

Reaction notes

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