6-Methoxy-8-quinolinamine → HCID 19592552, compound

HRID 613475Notes

Reaction equation

HRID 613475 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[Cl:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:16]=1[C:17](Cl)=[O:18].C(N(CC)CC)C>C(Cl)CCl.C(OCC)(=O)C>[Cl:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:16]=1[C:17]([NH:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2)=[O:18]

Participants

6

Reactant 3

HCID 70236-Methoxy-8-quinolinamineHCID 8471TriethylamineHCID 783922,6-Dichlorobenzoyl chloride

Product 1

HCID 19592552HCID 19592552, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 8-amino-6-methoxyquinoline (121 mg), 2,6-dichlorobenzoyl chloride (175 mg) and triethylamine (91.4 mg) in ethylene chloride (3 ml) was refluxed for 3 hours. After cooling, the mixture was diluted with ethyl acetate, washed with water, saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate:n-hexane, 1:2, v/v) to give 8-(2,6-dichlorobenzoylamino)-6-methoxyquinoline (164.5 mg).

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureAfter cooling
  3. washwashed with water, saturated sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record
ord-6b6d981532bd438c90d407cdbbdb2208
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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