Methanol → HCID 53753295, compound

HRID 1264238Notes

Reaction equation

HRID 1264238 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[N:7][C:6]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.OS(O)(=O)=O.[CH3:23]O>>[CH3:23][O:14][C:13](=[O:15])[C:12]1[CH:16]=[CH:17][C:9]([C:6]2[N:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 113566674-(6-methoxypyridazin-3-yl)benzoic Acid

Product 1

HCID 53753295HCID 53753295, compound

Conditions

Temperature
50 °C

Procedure

To a solution of 4-(6-methoxy-pyridazin-3-yl)-benzoic acid (5.02 g, 21.8 mmol) (reference example 11f) in methanol (75 mL) is added slowly conc. H2SO4 (3.75 mL). The resulting solution is heated to 50° C. and stirred for 1 hour. The solution is then concentrated to one third volume, cooled to 0°-5° C., adjusted to pH 6 with sat NaHCO3 soln and extracted into ethyl acetate. The organic layer is washed with brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (eluting with 20% ethyl acetate in dichloromethane) to give 4.26 g of title compound as a white crystalline solid. 1H NMR (DMSO) δ 3.90 (s, 3H), 4.10 (s, 3H), 7.38 (d, J=9 Hz, 1H), 8.10 (d, J=9 Hz, 2H), 8.25 (m, 3H). MS (EI) m/z 244 (M+).

Workup

  1. concentrationThe solution is then concentrated to one third volume
  2. temperaturecooled to 0°-5° C.
  3. extractionextracted into ethyl acetate
  4. washThe organic layer is washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue is purified by flash chromatography (eluting with 20% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-82d5b5a6badf4685aab6a8efb9b96aa9
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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