1-Chloroethyl chloroformate → 3-Chloro-5,6,7,8-tetrahydropyrido[3,4-c]pyridazine

HRID 1713147Notes

Reaction equation

HRID 1713147 reaction equation
C([N:8]1[CH2:17][CH2:16][C:15]2[CH:14]=[C:13]([Cl:18])[N:12]=[N:11][C:10]=2[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClC(Cl)C>[Cl:18][C:13]1[N:12]=[N:11][C:10]2[CH2:9][NH:8][CH2:17][CH2:16][C:15]=2[CH:14]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 57420585HCID 57420585, compound

Product 1

HCID 457896783-Chloro-5,6,7,8-tetrahydropyrido[3,4-c]pyridazine

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 7-benzyl-3-chloro-5,6,7,8-tetrahydropyrido[3,4-c]pyridazine (1.3 g, 5.0 mmol) and 1-chloroethyl chloroformate (0.86 g, 10.0 mmol) in dichloroethane (30 ml) is heated at refluxing temperature overnight. The solvent is removed in vacuo and MeOH (30 ml) is added to the residue. The resulting mixture is refluxed for 30 min. The solvent is removed in vacuo to give the title compound as a hydrogen chloride salt, which is used in the next step without purification.

Workup

  1. temperatureis heated
  2. temperatureat refluxing temperature overnight
  3. customThe solvent is removed in vacuo and MeOH (30 ml)
  4. additionis added to the residue
  5. temperatureThe resulting mixture is refluxed for 30 min
  6. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-e857032e0ef84804ad4a93c236c279a2
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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