Ammonia → 4-[(3-Bromophenyl)amino]-6,7-dimethoxy-3-quinolinecarboxamide

HRID 611996Notes

Reaction equation

HRID 611996 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:23]([OH:25])=O)[CH:5]=[CH:6][CH:7]=1.[NH3:26]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:23]([NH2:26])=[O:25])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 53288784-(3-Bromophenylamino)-6,7-dimethoxyquinoline-3-carboxylic Acid

Product 1

HCID 53288794-[(3-Bromophenyl)amino]-6,7-dimethoxy-3-quinolinecarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4.03 g of 4-[(3-bromophenyl)amino]-6,7-dimethoxy-3-quinolinecarboxylic acid, 3.24 g of carbonyldiimiazole, and 100 ml of dimethylformamide was heated at 55 for 30 m, cooled to 0° C., and saturated with ammonia gas. After warming to 25 the resulting solution was stirred for 45 m, heated at 50, and evaporated to remove dimethylformamide. The residue was stirred with water, and the resulting solid was filtered, washed with water, and dried. Recrystallization from acetone gave a grey solid, mp 239-242° C.

Workup

  1. temperaturewas heated at 55 for 30 m
  2. temperatureAfter warming to 25 the resulting solution
  3. temperatureheated at 50
  4. customevaporated
  5. customto remove dimethylformamide
  6. stirringThe residue was stirred with water
  7. filtrationthe resulting solid was filtered
  8. washwashed with water
  9. customdried
  10. customRecrystallization from acetone
  11. customgave a grey solid, mp 239-242° C.

Sources & evidence

ORD record
ord-1c5c6e904ea84bb0a9bc4984b6ae9d9e
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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