Ammonium Hydroxide → 3,6-Dichloropyridazine-4-carboxamide

HRID 869163Notes

Reaction equation

HRID 869163 reaction equation
[NH4+].[OH-].C([N:6](C(C)C)CC)(C)C.[Cl:12][C:13]1[N:14]=[N:15][C:16]([Cl:22])=[CH:17][C:18]=1[C:19](Cl)=[O:20]>C1COCC1.CN(C1C=CN=CC=1)C>[Cl:12][C:13]1[N:14]=[N:15][C:16]([Cl:22])=[CH:17][C:18]=1[C:19]([NH2:6])=[O:20]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 810183,6-Dichloropyridazine-4-carbonyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 2620493,6-Dichloropyridazine-4-carboxamideYield 96.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of NH4OH (1.1 mL, 17 mmol, 1.2 equiv) and diisopropylethylamine (6.2 mL, 36 mmol, 2.1 equiv) in THF (57 mL) was sonicated until homogeneous after which was added DMAP (1.0 g, 14 mmol, 1.0 equiv). 3,6-dichloropyridazine-4-carbonyl chloride (3.0 g, 14 mmol, 1.0 equiv) was then added and the solution was stirred at room temperature for 20 minutes. The solution was filtered and partitioned between EtOAc and 1M KHSO4 solution. The organic layer was washed once more with 1M KHSO4 and saturated NaCl, dried over Na2SO4, and evaporated to dryness to give the desired product (2.6 g, 96%).

Workup

  1. filtrationThe solution was filtered
  2. custompartitioned between EtOAc and 1M KHSO4 solution
  3. washThe organic layer was washed once more with 1M KHSO4 and saturated NaCl
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-d019315dba9342ab9d51e5345a0fc0a8
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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