Hydrazine hydrate (1:1) → Pyrido(2,3-d)pyridazine-5,8-diol

HRID 1166061Notes

Reaction equation

HRID 1166061 reaction equation
O.[NH2:2][NH2:3].[N:4]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:10](O[C:13](=[O:14])[C:5]=12)=[O:11].C([O-])(=O)C.[Na+]>C(O)(=O)C.O>[N:4]1[C:5]2[C:13](=[O:14])[NH:2][NH:3][C:10](=[O:11])[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 69688Furo[3,4-b]pyridine-5,7-dioneHCID 517045Sodium Acetate

Product 1

HCID 220711Pyrido(2,3-d)pyridazine-5,8-diolYield 76.2%

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

Hydrazine hydrate (13.09 g, 0.261 mol) was added to a stirred solution of pyridine-2,3-dicarboxylic anhydride (30.0 g, 0.201 mol) and sodium acetate (21.45 g, 0.261 mol) in 40% acetic acid/water (400 ml). The reaction was heated at reflux for 3 days under nitrogen. The yellow precipitate was filtered off and washed successively with water (4×200 ml), hexane (3×150 ml) and diethyl ether (3×150 ml) to give the title-compound (25.0 g, 76%), 1H NMR (250 MHz, d6-DMSO) δ 7.90 (1H, q, J=4.5Hz, Ar—H), 8.51 (1H, d, J=4.5Hz, Ar—H), 9.13 (1H, d, J=4.6Hz, Ar—H), 11.65 (2H, br s, 2 of NH); MS (ES+) m/e 164 [MH]+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 3 days under nitrogen
  3. filtrationThe yellow precipitate was filtered off
  4. washwashed successively with water (4×200 ml), hexane (3×150 ml) and diethyl ether (3×150 ml)

Sources & evidence

ORD record
ord-4090e406b46f422aa0e5063089bcee0a
Source dataset
uspto-grants-2003_09
Patent number
US06613766B1

Reaction notes

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