Methanol → HCID 18694241, compound

HRID 1870892Notes

Reaction equation

HRID 1870892 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1.OS(O)(=O)=O.[CH3:26]O>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([O:16][CH3:26])=[O:15])=[CH:12][CH:13]=2)=[C:4]([C:17]([F:18])([F:19])[F:20])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 18694229HCID 18694229, compound

Product 1

HCID 18694241HCID 18694241, compoundYield 50%

Procedure

Crude 4'-amino-2'-trifluoromethylbiphenyl-4-carboxylic acid (D33, 0.31 g, 0.078 mol) was dissolved in methanol (200 ml) and treated with conc. H2SO4 acid (1 ml). The mixture was heated at reflux under argon for 2 hrs, then concentrated in vacuo. The resultant yellow solid was basified with 10% aqueous Na2CO3 solution, extracted with dichloromethane, then the extract dried (Na2SO4) and concentrated in vacuo. The resultant yellow solid was purified by preparative TLC on silica gel plates eluting with 1:1 pet ether/ether to afford the title compound as an off-white solid (161 mg, 50%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux under argon for 2 hrs
  3. concentrationconcentrated in vacuo
  4. extractionextracted with dichloromethane
  5. dry with materialthe extract dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resultant yellow solid was purified by preparative TLC on silica gel plates
  8. washeluting with 1:1 pet ether/ether

Sources & evidence

ORD record
ord-672b62354b0447eeb3594a6b22b5aa1f
Source dataset
uspto-grants-2000_08
Patent number
US06100272

Reaction notes

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