6-Bromo-5-hydroxy-2h-3,1-benzoxazine-2,4(1h)-dione → Methyl 6-amino-3-bromo-2-hydroxybenzoate

HRID 1725961Notes

Reaction equation

HRID 1725961 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=O)[O:8][C:7](=[O:12])[C:6]=2[C:13]=1[OH:14]>CO>[NH2:10][C:5]1[C:6]([C:7]([O:8][CH3:9])=[O:12])=[C:13]([OH:14])[C:2]([Br:1])=[CH:3][CH:4]=1

Participants

3

Reactant 1

HCID 876051196-Bromo-5-hydroxy-2h-3,1-benzoxazine-2,4(1h)-dione

Product 1

HCID 66685945Methyl 6-amino-3-bromo-2-hydroxybenzoateYield 29.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of Example 385C (˜18 g) in methanol (400 mL) was heated to reflux for 2 hours and then purified on a silica gel column with 20% ethyl acetate in hexanes to provide the desired product (3.95 g, 29.8% yield for three steps). 1H NMR (DMSO-d6) δ 3.90 (s, 3H), 6.22 (d, 1H), 6.60 (s, 2H), 7.30 (d, 1H), 11.70 (s, 1H); MS (DCI/NH3) m/e 246, 248 (M+H)+.

Workup

  1. temperatureto reflux for 2 hours
  2. custompurified on a silica gel column with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-7eb4b356b5e64842aba9269a86a81757
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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