Methanol → Methyl 4'-amino-2'-methyl[1,1'-biphenyl]-4-carboxylate

HRID 1870877Notes

Reaction equation

HRID 1870877 reaction equation
S(Cl)(Cl)=O.[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([OH:20])=[O:19])=[CH:14][CH:13]=2)=[C:8]([CH3:21])[CH:7]=1.[CH3:22]O>>[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([O:20][CH3:22])=[O:19])=[CH:16][CH:17]=2)=[C:8]([CH3:21])[CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 18694306HCID 18694306, compound

Product 1

HCID 21948355Methyl 4'-amino-2'-methyl[1,1'-biphenyl]-4-carboxylateYield 89%

Procedure

Thionyl chloride (10 ml) was added dropwise and cautiously to methanol (200 ml) with stirring. 4'-Amino-2'-methylbiphenyl-4-carboxylic acid (D1) (8.44 g, 37 mmol) was added, and the mixture was then stirred at reflux for 3 h. Solvent was then removed in vacuo to yield the title compound (9.16 g, 89%) as the hydrochloride salt.

Workup

  1. stirringthe mixture was then stirred
  2. temperatureat reflux for 3 h
  3. customSolvent was then removed in vacuo

Sources & evidence

ORD record
ord-89baabbab9574addb2d187c4d6b3d6a8
Source dataset
uspto-grants-2000_08
Patent number
US06100272

Reaction notes

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