Hydrochloric Acid → 2-(4-Fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid

HRID 1676293Notes

Reaction equation

HRID 1676293 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]/[N:9]=[CH:10]/[CH:11]=[C:12]2[C:17](=[O:18])[O:16]C(C)(C)[O:14][C:13]2=O)=[CH:4][CH:3]=1.C[O-].[Na+].Cl.C(Cl)Cl>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]([C:17]([OH:16])=[O:18])=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 10942334Sodium MethoxideHCID 87314859HCID 87314859, compound

Product 1

HCID 667671712-(4-Fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acidYield 87.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (E)-5-(2-(2-(4-fluorophenyl)hydrazono)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (0.60 g, 2.05 mmol) and NaOMe (0.133 g, 2.46 mmol) in MeOH (10 mL) was heated under reflux for 15 hours. The salt was treated with cold 1 N HCl solution, extrated with CH2Cl2, dried over MgSO4, and concentrated to afford 0.42 g (87%) of the desired product. 1H NMR (400 MHz, CDCl3) δ 13.57 (br s, 1H), 8.29 (m, 2H), 7.63 (m, 2H), 7.24 (m, 2H); 19F NMR (376 MHz, CDCl3) δ −110.7. LRMS (ESI pos) m/e 235.1 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-55c4368816614993bf3c057c3f41fbde
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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