Ammonia → 6-Chloropyridazine-3-carboxamide

HRID 840304Notes

Reaction equation

HRID 840304 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([O:10]CCCC)=O)=[CH:4][CH:3]=1.[NH3:15]>C1COCC1>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([NH2:15])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 22622489Butyl 6-chloropyridazine-3-carboxylate

Product 1

HCID 125775576-Chloropyridazine-3-carboxamideYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the chloro pyridazine compound from the previous step (51 g, 0.238 mole) in THF (375 ml) was treated with methanolic ammonia (saturated, 80 ml). The reaction was allowed to stand at ambient temperature overnight. The precipitate was filtered and dried to give 6-chloropyridazine-3-carboxamide as a pink solid (18.2 g, 49%). [Further material could be obtained by evaporating the filtrate (at reduced pressure) and treating the residue with THF (100 ml) and methanolic ammonia (40 ml). The product was isolated as before to give a pink solid (17.4 g). Total yield (35.6 g, 95%)].

Workup

  1. filtrationThe precipitate was filtered
  2. customdried

Sources & evidence

ORD record
ord-4085cbd114354e3a8b67dff63e08b7d2
Source dataset
uspto-grants-2002_04
Patent number
US06365603B1

Reaction notes

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