5-Hydroxy-1H-benzo[d][1,3]oxazine-2,4-dione → Methyl 2-amino-6-hydroxybenzoate

HRID 1725964Notes

Reaction equation

HRID 1725964 reaction equation
[OH:1][C:2]1[C:7]2[C:8](=[O:13])[O:9][C:10](=O)[NH:11][C:6]=2[CH:5]=[CH:4][CH:3]=1>CO>[NH2:11][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([OH:1])[C:7]=1[C:8]([O:9][CH3:10])=[O:13]

Participants

3

Reactant 1

HCID 542193185-Hydroxy-1H-benzo[d][1,3]oxazine-2,4-dione

Product 1

HCID 21514499Methyl 2-amino-6-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of Example 386A (1.0 g, 5.6 mmol) and methanol (40 mL) was heated to reflux for 6 hours, concentrated, and purified on a silica gel column eluting with 30% ethyl acetate in hexanes to provide the desired product, 0.81 g, 86.6%. 1H NMR (DMSO-d6) δ 3.88 (s, 3H), 5.95 (d, 1H), 6.20 (d, 1H), 6.34 (s, 214), 7.02 (t, 1H), 10.88 (s, 1H); MS (DCI/NH3): m/e 168 (M+H)+.

Workup

  1. temperatureto reflux for 6 hours
  2. concentrationconcentrated
  3. custompurified on a silica gel column
  4. washeluting with 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-8992cee931104ba2a049fd3ea682597f
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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