(4-Chlorophenyl)hydrazine → HCID 72557542, compound

HRID 2220198Notes

Reaction equation

HRID 2220198 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=O)=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][NH2:20])=[CH:15][CH:14]=1>C(O)C.C(O)(=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[N:20][NH:19][C:16]2[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH:15]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 70624(4-Chlorophenyl)hydrazineHCID 1397781-Indanone, 6-bromo-

Product 1

HCID 72557542HCID 72557542, compoundYield 101.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 6-Bromo-indan-1-one (0.58 g, 2.7 mmole) in ethyl alcohol (5 mL) was added (4-Chloro-phenyl)-hydrazine (0.492 g, 2.7 mmole) and 5 drops of acetic acid. The reaction mixture was refluxed for 30 minutes then cooled to room temperature. The resulting solid precipitate was filtered and washed with ice cold methanol to give N-(6-Bromo-indan-1-ylidene)-N′-(4-chloro-phenyl)-hydrazine (0.92 gm, 100%). HPLC Rt=4.69 min. m/z=335 (M+H+).

Workup

  1. temperatureThe reaction mixture was refluxed for 30 minutes
  2. filtrationThe resulting solid precipitate was filtered
  3. washwashed with ice cold methanol

Sources & evidence

ORD record
ord-90df0b48e84f452188df3d3c7c3e5547
Source dataset
uspto-grants-2008_08
Patent number
US07417040B2

Reaction notes

Loading…