Sodium Carbonate → 2-(Acetamido)-5-methoxy-4-phenylbenzoic acid

HRID 454503Notes

Reaction equation

HRID 454503 reaction equation
[C:1]1(OB=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10](=[O:13])([O-])[O-:11].[Na+].[Na+].Br[C:17]1[C:28]([O:29][CH3:30])=[CH:27][C:20]2C(=O)[O:22][C:23]([CH3:25])=[N:24][C:19]=2[CH:18]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C.O.COCCOC>[C:23]([NH:24][C:19]1[CH:18]=[C:17]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:28]([O:29][CH3:30])=[CH:27][C:20]=1[C:10]([OH:11])=[O:13])(=[O:22])[CH3:25]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 14438906HCID 14438906, compoundHCID 669902127-bromo-6-methoxy-2-methyl-4H-3,1-benzoxazin-4-one

Product 1

HCID 669909442-(Acetamido)-5-methoxy-4-phenylbenzoic acidYield 63.9%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Water (1.2 mL), phenylboranic acid (0.22 g), sodium carbonate (0.38 g), and bis(triphenylphosphine)palladium(II) dichloride (21 mg) were added to an ethylene glycol dimethyl ether (4 mL) suspension of the obtained 7-bromo-6-methoxy-2-methyl-4H-3,1-benzoxazin-4-one (0.40 g), followed by heating to reflux under a nitrogen atmosphere for 4 hours and 30 minutes. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added thereto. The aqueous layer was separated, and the organic layer was extracted with a 2 mol/L aqueous solution of sodium hydroxide. The aqueous layer and the extract were combined. The resulting mixture was adjusted to a pH of 1 with 6 mol/L hydrochloric acid, and ethyl acetate was added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the obtained residue, and the solid substance was collected by filtration to obtain 0.27 g of 2-(acetamido)-5-methoxy-4-phenylbenzoic acid as a yellow solid.

Workup

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 4 hours and 30 minutes
  3. customThe aqueous layer was separated
  4. extractionthe organic layer was extracted with a 2 mol/L aqueous solution of sodium hydroxide
  5. additionwas added
  6. customThe organic layer was separated
  7. washwashed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. additionDiisopropyl ether was added to the obtained residue
  11. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-69f7d1f43be4451881c965c4a249cb54
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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