Ammonia → 6-Chloropyridazine-3-carboxamide

HRID 492586Notes

Reaction equation

HRID 492586 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([O:10]C)=O)=[CH:4][CH:3]=1.[NH3:12]>CO>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([NH2:12])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 12379801Methyl 6-chloropyridazine-3-carboxylate

Product 1

HCID 125775576-Chloropyridazine-3-carboxamideYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve methyl 6-chloropyridazine-3-carboxylate (0.498 g, 2.89 mmol) in methanol (28 mL). Cool the solution to 0° C. with an acetone/dry ice bath. Bubble ammonia into the reaction mixture then allow it to warm to 0° C. over 1 hour before concentrating to give the title compound (0.451 g, 99%): TOF MS ES+ 157.0 (M)+, HRMS calcd for C5H4N3OCl 157.0043 (M)+, found 157.0010, time 4.45 min; HPLC [YMC-Pro pack C-18 (150×4.6 mm, S-5 microm), 0.1 TFA/acetonitrile in 0.1% TFA/water at 1.0 mL/min, 10-20% over 5 min then 20-95% over 18], tR=5.2 min, 100% purity.

Workup

  1. temperatureto warm to 0° C. over 1 hour
  2. concentrationbefore concentrating

Sources & evidence

ORD record
ord-e3576933a4e4450f92eeb73493540ac5
Source dataset
uspto-grants-2009_05
Patent number
US07531557B2

Reaction notes

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