Ethyl 6-chloropyridazine-3-carboxylate → HCID 19006951, compound

HRID 1742582Notes

Reaction equation

HRID 1742582 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.[CH3:13][O:14][C:15](=[O:27])[C:16]1[CH:25]=[CH:24][C:23]([NH2:26])=[C:18]([C:19](OC)=[O:20])[CH:17]=1>C(Cl)(Cl)Cl>[O:20]=[C:19]1[C:18]2[CH:17]=[C:16]([C:15]([O:14][CH3:13])=[O:27])[CH:25]=[CH:24][C:23]=2[N:26]=[C:2]2[CH:3]=[CH:4][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:6][N:7]12

Participants

4

Reactant 2

HCID 10352425Ethyl 6-chloropyridazine-3-carboxylateHCID 11095854Dimethyl 4-aminoisophthalate

Product 1

HCID 19006951HCID 19006951, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of ethyl 6-chloro-3-pyridazinecarboxylate (0.29 g, 1.55 mmol, Example 1, Step A) and dimethyl 4-aminoisophthalate (0.36 g, 1.72 mmol, Example 1, Step B) was heated as a melt at 165°-170° C. for 30 min. The oil was dissolved into chloroform, washed with 10% ammonium hydroxide solution, dried (MgSO4) , filtered and concentrated. Medium pressure chromatography (silica gel, chloroform to 1% methanol in chloroform) of the crude oily-solid afforded 2-ethyl 8-methyl 10-oxo-10H-pyridazino[6,1-b]quinazoline-2,8-dicarboxylate as a yellow solid, mp 218°-221° C. dec.

Workup

  1. temperaturewas heated as a melt at 165°-170° C. for 30 min
  2. washwashed with 10% ammonium hydroxide solution
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c691b7aae3a441a4b7e2521cc32907df
Source dataset
uspto-grants-1994_08
Patent number
US05340808

Reaction notes

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