2-(Acetamido)-5-methoxy-4-phenylbenzoic acid → 2-Amino-5-methoxy-4-phenylbenzoic acid

HRID 454504Notes

Reaction equation

HRID 454504 reaction equation
C([NH:4][C:5]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([O:20][CH3:21])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=O)C>O1CCOCC1.Cl>[NH2:4][C:5]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([O:20][CH3:21])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 669909442-(Acetamido)-5-methoxy-4-phenylbenzoic acid

Product 1

HCID 669901042-Amino-5-methoxy-4-phenylbenzoic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution mixture of 2-(acetamido)-5-methoxy-4-phenylbenzoic acid (0.41 g) in dioxane (1.2 mL) and concentrated hydrochloric acid (1.2 mL) was heated to reflux for 3 hours and 40 minutes. After cooling the reaction mixture to room temperature, the solvent was evaporated under reduced pressure, and water was added to the residue. After adjusting the pH to 7 with a 1 mol/L aqueous solution of sodium hydroxide, chloroform was added thereto. The organic layer was separated and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain 2-amino-5-methoxy-4-phenylbenzoic acid as a brown solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours and 40 minutes
  3. customthe solvent was evaporated under reduced pressure, and water
  4. additionwas added to the residue
  5. additionwas added
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-017f679b6a0f49e08390cde7890923b9
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

Loading…