Methanol → HCID 11964599, compound

HRID 906630Notes

Reaction equation

HRID 906630 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[C:8]([C:15]2[N:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OS(O)(=O)=O.[CH3:26]O>>[CH3:26][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([C:15]2[N:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[C:9]([C:11]([F:12])([F:13])[F:14])=[CH:10][C:2]=1[NH2:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 58532846HCID 58532846, compound

Product 1

HCID 11964599HCID 11964599, compoundYield 46%

Conditions

Temperature
110 °C

Procedure

2-Amino-5-pyridazin-3-yl-4-trifluoromethyl-benzoic acid (165 mg, 0.583 mmol) was dissolved in MeOH (15 mL). Concd H2SO4 (360 μL) was added and solution was heated to 110° C. for 11.5 h. The solution was concentrated in vacuo and the residue was dissolved in water (2 mL). The aqueous layer was neutralized with aq NaOH (2 N) and extracted with DCM. The organic phase was washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, EtOAc/hexanes (1:4 to 1:1)) to give the title compound (79 mg, 46%). API-ES: m/z 298.1 [M+H]+, rt 3.48 min

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe residue was dissolved in water (2 mL)
  3. extractionextracted with DCM
  4. washThe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (silica gel, EtOAc/hexanes (1:4 to 1:1))

Sources & evidence

ORD record
ord-6fad93bd7e974f4d9b6f1de2275ff34a
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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