Sodium Hydroxide → Methyl 2-amino-3-methoxybenzoate

HRID 1186091Notes

Reaction equation

HRID 1186091 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[NH:9][C:10](=O)[O:11][C:12](=[O:13])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>CO.C(OCC)(=O)C>[NH2:9][C:8]1[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=1[C:12]([O:11][CH3:10])=[O:13]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 105596798-Methoxy-1H-benzo[d][1,3]oxazine-2,4-dione

Product 1

HCID 602320Methyl 2-amino-3-methoxybenzoateYield 101%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 8-methoxy-1H-benzo[d][1,3]oxazine-2,4-dione (0.8 g, 4.1 mmol) in anhydrous methanol (25 mL), was added sodium hydroxide (0.24 g, 4.1 mmol) and the mixture was heated to reflux for 2 hours. The solution was cooled, diluted with ethyl acetate, washed with water, saturated sodium bicarbonate, then brine, and dried with sodium sulfate. It was filtered and concentrated to yield methyl 2-amino-3-methoxybenzoate (750 mg, 100%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperatureThe solution was cooled
  4. washwashed with water, saturated sodium bicarbonate
  5. dry with materialbrine, and dried with sodium sulfate
  6. filtrationIt was filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8f957ffe94ac44e29d0f38114cd328ba
Source dataset
uspto-grants-2014_03
Patent number
US08673897B2

Reaction notes

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