4-Cyanophenylhydrazine Hydrochloride → Cyclopropanecarboxylic acid(6-cyano-2,3,4,9-tetrahydro-1h-carbazol-3-yl)amide

HRID 545570Notes

Reaction equation

HRID 545570 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]([CH:11]2[CH2:13][CH2:12]2)=[O:10])[CH2:4][CH2:3]1.Cl.[C:15]([C:17]1[CH:22]=[CH:21][C:20]([NH:23]N)=[CH:19][CH:18]=1)#[N:16]>>[C:15]([C:17]1[CH:18]=[C:19]2[C:20](=[CH:21][CH:22]=1)[NH:23][C:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]([CH:11]3[CH2:13][CH2:12]3)=[O:10])[CH2:4][C:3]2=1)#[N:16]

Participants

3

Reactant 2

HCID 162129624-Cyanophenylhydrazine HydrochlorideHCID 43652864N-(4-oxocyclohexyl)cyclopropanecarboxamide

Product 1

HCID 59161240Cyclopropanecarboxylic acid(6-cyano-2,3,4,9-tetrahydro-1h-carbazol-3-yl)amide

Procedure

Prepare the title compound from cyclopropanecarboxylic acid(4-oxocyclohexyl)amide (51.3 g, 283 mmol) and 4-cyanophenylhydrazine hydrochloride (48.0 g, 283 mmol) by essentially following procedures as described in Preparation 3 to obtain 57.0 g (72%) of a pale yellow solid. mp: 231-233° C.; MS (ES): m/z 280 (M+1).

Sources & evidence

ORD record
ord-c726b969fece48519170a5cd476219fd
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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