Lithium Hydroxide → 6-(6-Chloro-2-methyl-3-oxo-2,3-dihydropyridazin-4-ylamino)nicotinic acid

HRID 449663Notes

Reaction equation

HRID 449663 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=[O:16])=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1.[OH-].[Li+].C(OCC)(=O)C.[Cl-].[NH4+]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([OH:17])=[O:16])=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1

Participants

5

Reactant 3

HCID 3939Lithium Hydroxide2×HCID 57662841Methyl 6-(6-Chloro-2-methyl-3-oxo-2,3-dihydropyridazin-4-ylamino)nicotinateHCID 86583716Ammonium chloride ethyl acetate

Product 1

HCID 667425116-(6-Chloro-2-methyl-3-oxo-2,3-dihydropyridazin-4-ylamino)nicotinic acidYield 77.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 6-(6-chloro-2-methyl-3-oxo-2,3-dihydropyridazin-4-ylamino)nicotinate (1.523 g, 5.17 mmol, Eq: 1.00) was suspended in dioxane (90 ml). 1 M Lithium hydroxide (10.3 ml, 10.3 mmol, Eq: 2) was added dropwise. The light brown suspension was stirred overnight at room temperature. 1 M Lithium hydroxide (10.3 ml, 10.3 mmol, Eq: 2) was added again and stirred over the weekend. A mixture of ethyl acetate/ammonium chloride solution was added to the reaction mixture. The resulting precipitate was collected by filtration. The precipitate was triturated with water (200 ml), filtered, washed with ethyl acetate and dried in vacuo to give a light yellow solid (1.13 g). (M+H)+=278.8 m/e

Workup

  1. stirringstirred over the weekend
  2. additionwas added to the reaction mixture
  3. filtrationThe resulting precipitate was collected by filtration
  4. customThe precipitate was triturated with water (200 ml)
  5. filtrationfiltered
  6. washwashed with ethyl acetate
  7. customdried in vacuo

Sources & evidence

ORD record
ord-e48053e3868b45b4bff945c585bda0c9
Source dataset
uspto-grants-2013_07
Patent number
US08481540B2

Reaction notes

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