Ethyl chloroformate → 8-(2,6-Dichlorobenzoylamino)-4-(2-ethoxycarbonylhydrazino)quinoline

HRID 613550Notes

Reaction equation

HRID 613550 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].Cl[C:25]([O:27][CH2:28][CH3:29])=[O:26]>N1C=CC=CC=1.ClCCl>[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][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:5]

Participants

5

Reactant 2

HCID 10928Ethyl chloroformateHCID 19592850HCID 19592850, compound

Product 1

HCID 195928108-(2,6-Dichlorobenzoylamino)-4-(2-ethoxycarbonylhydrazino)quinolineYield 47.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 8-(2,6-dichlorobenzoylamino)-4-hydrazinoquinoline (200 mg) in pyridine (2 ml) was added a solution of ethyl chloroformate (68.8 mg) in dichloromethane (0.5 ml) under ice-cooling, and the mixture was stirred for 1 hour at ambient temperature. The mixture was concentrated in vacuo, and the residue was diluted with dichloromethane. The mixture was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from ethanol to give 8-(2,6-dichlorobenzoylamino)-4-(2-ethoxycarbonylhydrazino)quinoline (115 mg).

Workup

  1. temperaturecooling
  2. concentrationThe mixture was concentrated in vacuo
  3. additionthe residue was diluted with dichloromethane
  4. washThe mixture was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-472603c746d749ac9556540b0217cb08
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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