Diethyl Ether → 6-(2'-Chlorocinnamoyl)amino-4-methoxy-2-methyl-quinoline

HRID 580811Notes

Reaction equation

HRID 580811 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6](Cl)=[O:7].[NH2:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[N:20]=[C:19]([CH3:24])[CH:18]=[C:17]2[O:25][CH3:26].CCOCC>C(O)(=O)C>[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([NH:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[N:20]=[C:19]([CH3:24])[CH:18]=[C:17]2[O:25][CH3:26])=[O:7]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2737382HCID 2737382, compoundHCID 151333914-Methoxy-2-methylquinolin-6-amine

Product 1

HCID 536780766-(2'-Chlorocinnamoyl)amino-4-methoxy-2-methyl-quinoline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 2-chlorocinnamoyl chloride (prepared by treatment of 2-chlorocinnamic acid with oxalyl cloride and catalytic DMF in dichloromethane) (0.27 gm) in 1 mL acetic acid was added to a solution of 6-amino-4-methoxy-2-methyl-quinoline (0.25 g, 1.33 mmol) in glacial acetic acid (3 mL). A heavy precipitate formed, and the mixture was stirred for 1 h at room temperature. Ether (25 mL) was added and the solid was filtered, washed with ether, and dried by suction. The hydrochloride salt was suspended in warm water (25 mL) and ethanol (25 mL) and heated until dissolved. After cooling to room temperature, 5N sodium hydroxide was added to give a white precipitate that was filtered, and washed with water. Recrystallization from ethanol afforded the title compound; yield 0.27 g (58%); m.p. 228-229°; MS (FAB): m/z 353 (M+1).

Workup

  1. customA heavy precipitate formed
  2. filtrationthe solid was filtered
  3. washwashed with ether
  4. customdried by suction
  5. temperatureethanol (25 mL) and heated
  6. dissolutionuntil dissolved
  7. temperatureAfter cooling to room temperature
  8. addition5N sodium hydroxide was added
  9. customto give a white precipitate that
  10. filtrationwas filtered
  11. washwashed with water
  12. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-f3bd4a11a0aa45219b08e67d8159804e
Source dataset
uspto-grants-1999_07
Patent number
US05919776

Reaction notes

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