Water → Methyl 2-amino-6-methoxybenzoate

HRID 1449562Notes

Reaction equation

HRID 1449562 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 (Na2SO4), 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. dry with materialthe combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6cae1c3572a0406a9de07c803c0d2b27
Source dataset
uspto-grants-1997_02
Patent number
US05599814

Reaction notes

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