Ethyl chloroformate → HCID 178418827, compound

HRID 8240

Reaction equation

HRID 8240 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=[N:19][NH2:20])[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][CH:10]=1.Cl[C:22](OCC)=[O:23]>N1C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=[CH:11][CH:10]=2)=[C:22]([OH:23])[NH:20][N:19]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 73858327(1-Pyridin-2-yl-2-quinolin-4-yl-ethylidene)-hydrazine

Product 1

HCID 178418827HCID 178418827, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (1-pyridin-2-yl-2-quinolin-4-yl-ethylidene)-hydrazine (2.0 g, 7.6 mmol) in pyridine (20 mL) at 0° C. is added ethyl chloroformate (2 mL) dropwise. The mixture is warmed to room temperature and stirred for 2 h. The solution is refluxed for 12 h and concentrated in vacuo. The residue is treated with dichloromethane/methanol and the precipitate collected by vacuum filtration. The precipitate is triturated with ethanol to yield the title compound, 300 mg (13%), as a white solid.

Workup

  1. temperatureThe solution is refluxed for 12 h
  2. concentrationconcentrated in vacuo
  3. additionThe residue is treated with dichloromethane/methanol
  4. filtrationthe precipitate collected by vacuum filtration
  5. customThe precipitate is triturated with ethanol

Sources & evidence

ORD record
ord-c51fe6fbce314d199d31f9750821f276
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Linked notes

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