Methanol → Methyl 2-amino-5-methoxy-4-phenylbenzoate

HRID 454524Notes

Reaction equation

HRID 454524 reaction equation
S(=O)(=O)(O)O.CO.[NH2:8][C:9]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([O:24][CH3:25])=[CH:14][C:10]=1[C:11]([OH:13])=[O:12].[C:26](=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[NH2:8][C:9]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([O:24][CH3:25])=[CH:14][C:10]=1[C:11]([O:13][CH3:26])=[O:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 669901042-Amino-5-methoxy-4-phenylbenzoic acid

Product 1

HCID 66990992Methyl 2-amino-5-methoxy-4-phenylbenzoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Under ice-cooling, concentrated sulfuric acid (1 mL) was added to a methanol (10 mL) suspension of the obtained 2-amino-5-methoxy-4-phenylbenzoic acid, followed by heating to reflux for 6 hours. The reaction mixture was cooled to room temperature and was adjusted to a pH of 8.0 with a saturated aqueous solution of sodium bicarbonate, and chloroform was added thereto. The organic layer was separated and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Hexane was added to the obtained residue, and the solid substance was collected by filtration to obtain 0.24 g of methyl 2-amino-5-methoxy-4-phenylbenzoate as a brown solid.

Workup

  1. temperatureUnder ice-cooling
  2. temperatureby heating
  3. temperatureto reflux for 6 hours
  4. additionwas added
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. additionHexane was added to the obtained residue
  9. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-234444f3eb9b4ebfa885bf98bb654b81
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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