Pyridine → HCID 5328837, compound

HRID 611995Notes

Reaction equation

HRID 611995 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)([O:3][CH2:4][CH3:5])=[O:2].[Br:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25].N1C=CC=CC=1>C(O)C>[Br:21][C:22]1[CH:23]=[C:24]([NH:25][C:15]2[C:14]3[C:9](=[CH:10][C:11]([O:19][CH3:20])=[C:12]([O:17][CH3:18])[CH:13]=3)[N:8]=[CH:7][C:6]=2[C:1]([O:3][CH2:4][CH3:5])=[O:2])[CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 115623-BromoanilineHCID 103571783-Carbethoxy-4-chloro-6,7-dimethoxylquinoline

Product 1

HCID 5328837HCID 5328837, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 14.8 g of 3-carbethoxy-4-chloro-6,7-dimethoxylquinoline, 9.46 g of 3-bromoaniline, 4.05 ml of pyridine, and 150 ml of ethanol was refluxed for 30 min, evaporated to remove ethanol, and partitioned with dichloromethane-aq sodium bicarbonate. The organic layer was washed with water, dried, and concentrated. The residue was recrystallized from ethanol to give a white solid, mp 155-158° C.

Workup

  1. temperaturewas refluxed for 30 min
  2. customevaporated
  3. customto remove ethanol
  4. custompartitioned with dichloromethane-aq sodium bicarbonate
  5. washThe organic layer was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was recrystallized from ethanol
  9. customto give a white solid, mp 155-158° C.

Sources & evidence

ORD record
ord-a623c673d8a0494aa4b9b2ed9b8d4cd0
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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