Hydrochloric Acid → 4-chloro-1,3,8-trimethyl-1H,6H-pyrido[2,3-d]pyridazine-2,5-dione

HRID 2111107Notes

Reaction equation

HRID 2111107 reaction equation
[C:1]([C:4]1[N:5]([CH3:16])[C:6](=[O:15])[C:7]([CH3:14])=[C:8]([Cl:13])[C:9]=1[C:10](O)=[O:11])(=O)[CH3:2].O.[NH2:18][NH2:19].Cl>C1COCC1.C(OCC)(=O)C>[Cl:13][C:8]1[C:9]2[C:10](=[O:11])[NH:19][N:18]=[C:1]([CH3:2])[C:4]=2[N:5]([CH3:16])[C:6](=[O:15])[C:7]=1[CH3:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 666739552-Acetyl-4-chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid

Product 1

HCID 666733724-chloro-1,3,8-trimethyl-1H,6H-pyrido[2,3-d]pyridazine-2,5-dione

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-acetyl-4-chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid (1 equivalent) and hydrazine monohydrate (3.30 equivalents) in THF is added 1 N HCl (0.80 equivalents). After 16 hours, the reaction mixture is diluted with ethyl acetate, washed with water and brine, dried (MgSO4) and concentrated under reduced pressure. The desired product purified by trituration or flash column chromatography to afford the desired product as necessary.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe desired product purified by trituration or flash column chromatography

Sources & evidence

ORD record
ord-989346f730eb41e2bf962992f3b8d95f
Source dataset
uspto-grants-2009_04
Patent number
US07517994B2

Reaction notes

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