Water → Methyl 2-amino-6-methoxybenzoate

HRID 1598613Notes

Reaction equation

HRID 1598613 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[C:10]2[C:11](=[O:16])[O:12][C:13](=O)[NH:14][C:9]=2[CH:8]=[CH:7][CH:6]=1.O>CO>[NH2:14][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]([O:4][CH3:3])[C:10]=1[C:11]([O:12][CH3:13])=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 107502955-Methoxy-2H-3,1-benzoxazine-2,4(1H)-dione

Product 1

HCID 12318577Methyl 2-amino-6-methoxybenzoateYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred solution of sodium hydroxide (0.06 g, 1.5 mM) in methanol (7 mL) under a nitrogen atmosphere was added 5-methoxy-2H-3,1-benzoxazine-2,4(1H)-dione (2.90 g, 15.0 mM). The reaction mixture was stirred at 65° C. for 14.5 hr, cooled to room temperature and poured into water. The resulting solution was extracted with ethyl acetate and the combined extracts were dried (Na2 SO4), filtered and concentrated to provide the title compound (2.55 g, 94%) as a tan oil; MS(CI): 182 (M+H).

Workup

  1. temperaturecooled to room temperature
  2. extractionThe resulting solution was extracted with ethyl acetate
  3. customthe combined extracts were dried (Na2 SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3012f5da28db489a852e89308c185d17
Source dataset
uspto-grants-1998_04
Patent number
US05739133

Reaction notes

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