Pyridine → HCID 19593053, compound

HRID 613582Notes

Reaction equation

HRID 613582 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][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][C:13]([Br:17])=[CH:12]2)=[O:5].[C:22](OC(=O)C)(=[O:24])[CH3:23].N1C=CC=CC=1>C(Cl)CCl.ClCCl>[C:22]([NH:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][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][C:13]([Br:17])=[CH:12]2)=[O:5])(=[O:24])[CH3:23]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 19592685HCID 19592685, compound

Product 1

HCID 19593053HCID 19593053, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 8-(2-aminobenzoylamino)-3-bromoquinoline (200 mg), acetic anhydride (71.6 mg) and pyridine (139 mg) in ethylene chloride (4 ml) was stirred for 20 hours at ambient temperature. The mixture was diluted with dichloromethane, washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was suspended in hot ethanol and allowed to cool to ambient temperature. The resulting precipitates were collected by filtration to give 8-(2-acetamidobenzoylamino)-3-bromoquinoline (200 mg) as yellow powder.

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. temperatureto cool to ambient temperature
  5. customThe resulting precipitates
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-cb6e153c24824060a3b2c9b53e1152bc
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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