Dichloromethane → HCID 19592886, compound

HRID 613547Notes

Reaction equation

HRID 613547 reaction equation
ClC1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[C:12]2[NH:17][NH:18][CH3:19])=[O:5].C(N(CC)CC)C.[C:32](OC(=O)C)(=[O:34])[CH3:33].Cl[CH2:40][Cl:41]>>[C:32]([N:18]([CH3:19])[NH:17][C:12]1[C:11]2[C:16](=[C:7]([NH:6][C:4](=[O:5])[C:3]3[C:20]([Cl:24])=[CH:21][CH:22]=[CH:23][C:40]=3[Cl:41])[CH:8]=[CH:9][CH:10]=2)[N:15]=[CH:14][CH:13]=1)(=[O:34])[CH3:33]

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 19592531HCID 19592531, compound

Product 1

HCID 19592886HCID 19592886, compound

Procedure

To a stirred suspension of 8-(2,6-dichlorobenzoylamino)-4-(2-methylhydrazino)quinoline (500 mg) and triethylamine (700 mg) in dichloromethane (5 ml) was added acetic anhydride (155 mg) at ambient temperature, and the mixture was allowed to stand for 10 days at the same temperature. The mixture was diluted with dichloromethane, washed with water and evaporated in vacuo. The obtained residue was dissolved in methanol (10 ml), and a 28%0 solution of sodium methoxide in methanol (0.53 ml) was added thereto under ice-cooling. The mixture was stirred for 1 hour at the same temperature, and neutralized with 1N hydrochloric acid. The mixture was concentrated in vacuo and extracted with dichloromethane. The organic layer was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate) and crystallized from ethanol to give 4-(2-acetyl-2-methylhydrazino)-8-(2,6-dichlorobenzoylamino)quinoline (544 mg).

Workup

  1. washwashed with water
  2. customevaporated in vacuo
  3. dissolutionThe obtained residue was dissolved in methanol (10 ml)
  4. additiona 28%0 solution of sodium methoxide in methanol (0.53 ml) was added
  5. temperatureunder ice-cooling
  6. concentrationThe mixture was concentrated in vacuo
  7. extractionextracted with dichloromethane
  8. washThe organic layer was washed with water
  9. dry with materialdried over magnesium sulfate
  10. customevaporated in vacuo
  11. customThe residue was purified by column chromatography on silica gel (ethyl acetate)
  12. customcrystallized from ethanol

Sources & evidence

ORD record
ord-9017c3b4a0194bd28228a9651a4ed470
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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