diazo bis-(4-chloro-phenyl)-methane → HCID 10207626, compound

HRID 896705Notes

Reaction equation

HRID 896705 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]=[CH2:21])[CH:15]=3)[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)([CH3:3])[CH3:2].[N+](=[C:24]([C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)=[N-]>C1C=CC=CC=1>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([C:24]2([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)[CH2:21][CH:20]2[C:16]2[CH:15]=[C:14]([C:12]3[CH:13]=[C:4]([CH:1]([CH3:2])[CH3:3])[CH:5]=[C:6]4[C:11]=3[N:10]=[CH:9][CH:8]=[CH:7]4)[CH:19]=[CH:18][CH:17]=2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 11323003diazo bis-(4-chloro-phenyl)-methaneHCID 22350102HCID 22350102, compound

Product 1

HCID 10207626HCID 10207626, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
21 °C

Procedure

A solution of the 6-isopropyl-8-(3-vinyl-phenyl)-quinoline from Step 3 (230 mg, 0.84 mmol) and the diazo bis-(4-chloro-phenyl)-methane from Step 2 (530 mg, 2.0 mmol) in benzene (10 mL) was heated to reflux for 18 h, cooled to 21° C., and purified by flash chromatography (eluting with hexane/ethyl acetate, 90:10) to provide the 8-{3-[2,2-bis-(4-chloro-phenyl)-cyclopropyl]-phenyl}-6-isopropyl-quinoline compound as a yellow foam.

Workup

  1. temperatureto reflux for 18 h
  2. custompurified by flash chromatography (eluting with hexane/ethyl acetate, 90:10)

Sources & evidence

ORD record
ord-6173198e775645578c8dee28bff1645b
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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