Ammonia → 6-Chloropyridazine-3-carboxamide

HRID 1604373Notes

Reaction equation

HRID 1604373 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-afa0831777364122af345592699fd01a
Source dataset
uspto-grants-1999_11
Patent number
US05994353

Reaction notes

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