Formamide → 8-(2,6-Dichlorobenzoylamino)-4-(2-formylhydrazino)quinoline

HRID 613566Notes

Reaction equation

HRID 613566 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[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][NH2:18])=[O:5].[CH:24](N)=[O:25]>C(O)=O>[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[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][CH:24]=[O:25])=[O:5]

Participants

4

Reactant 2

HCID 713FormamideHCID 19592850HCID 19592850, compound

Product 1

HCID 195927348-(2,6-Dichlorobenzoylamino)-4-(2-formylhydrazino)quinolineYield 83.3%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a solution of 8-(2,6-dichlorobenzoylamino)-4-hydrazinoquinoline (200 mg) in formic acid (4 ml) was added formamide (26 mg), and the mixture was stirred at ambient temperature for 3 hours. The solvent was azeotropically removed with toluene. The residue was diluted with ethyl acetate, washed with water and saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate and concentrated in vacuo. The residual solid was treated with hot ethanol (2 ml), allowed to cool to ambient temperature, filtered and washed with ethanol to give 8-(2,6-dichlorobenzoylamino)-4-(2-formylhydrazino)quinoline (180 mg) as pale yellow crystal.

Workup

  1. customThe solvent was azeotropically removed with toluene
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with water and saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. additionThe residual solid was treated with hot ethanol (2 ml)
  7. temperatureto cool to ambient temperature
  8. filtrationfiltered
  9. washwashed with ethanol

Sources & evidence

ORD record
ord-465418af947342fa9aa5194a189f76fa
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

Loading…