2-Amino-5-chlorobenzoic acid → 8-Chloro-10-oxo-10H-pyridazino[6,1-b]quinazoline-2-carboxylic acid

HRID 1413422Notes

Reaction equation

HRID 1413422 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]([NH2:11])=[CH:4][CH:3]=1.Cl[C:13]1[N:18]=[N:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][CH:14]=1>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:13]3[CH:14]=[CH:15][C:16]([C:19]([OH:21])=[O:20])=[N:17][N:18]3[C:7](=[O:9])[C:6]=2[CH:10]=1

Participants

4

Reactant 2

HCID 124762-Amino-5-chlorobenzoic acidHCID 64157626-chloropyridazine-3-carboxylic Acid

Product 1

HCID 126656848-Chloro-10-oxo-10H-pyridazino[6,1-b]quinazoline-2-carboxylic acidYield 54.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5-chloroanthranilic acid (5.4 g, 31.6 mmol) and 6-chloropyridazine-3-carboxylic acid (5.0 g, 31.6 mmol) is heated at reflux in acetic acid (50 ml) for 80 hrs. The mixture is cooled and the precipitate which formes is collected to give 4.73 g of crude product, m.p. 253°-300° C. (dec.). Recrystallization of this material from pyridine gives the analytical material, m.p. 260°-262° C.

Workup

  1. temperatureis heated
  2. temperatureThe mixture is cooled
  3. customthe precipitate which formes is collected

Sources & evidence

ORD record
ord-82580a6fdd044ba4a9c07381fd01330b
Source dataset
uspto-grants-1981_02
Patent number
US04250177

Reaction notes

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