HCID 22249803, compound → HCID 22313198, compound

HRID 890229Notes

Reaction equation

HRID 890229 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([CH3:21])[C:8]([C:12]3[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[CH3:20])=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:22])[C:3]=1[CH2:23][CH2:24]Cl>NC(CC)CC.C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH2:7]([CH:6]([N:5]1[C:2]2[C:11]3[CH:10]=[CH:9][C:8]([C:12]4[C:13]([CH3:20])=[CH:14][C:15]([CH3:19])=[CH:16][C:17]=4[CH3:18])=[C:7]([CH3:21])[C:6]=3[N:5]=[C:4]([CH3:22])[C:3]=2[CH:23]=[CH:24]1)[CH2:11][CH3:10])[CH3:8]

Participants

5

Reactant 1

HCID 22249803HCID 22249803, compound

Product 1

HCID 22313198HCID 22313198, compoundYield 11.6%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolventHCID 120193-PentanamineSolvent

Procedure

A solution of 4-chloro-3-(2-chloroethyl)-7-mesityl-2,8-dimethylquinoline (200 mg, 0.54 mmol) in 3-aminopentane (6.0 mL) was stirred in a sealed tube at 200° C. for 8 hr. After evaporating, activated manganese dioxide (101 mg, 1.16 mmol) was added to a solution of the residue in toluene (9.0 mL) and the mixture was stirred for two days. After filtering through Celite, the mixture was evaporated. The residue was purified by silica gel column chromatography (10% ethyl acetate/hexane) to give the title compound (12 mg) as white crystals.

Workup

  1. customAfter evaporating
  2. filtrationAfter filtering through Celite
  3. customthe mixture was evaporated
  4. customThe residue was purified by silica gel column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8df8f41234cc4cb18fef70749ea5baf9
Source dataset
uspto-grants-2006_02
Patent number
US06995163B2

Reaction notes

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