Aluminum(III) Chloride → 5-Hydroxy-1H-benzo[d][1,3]oxazine-2,4-dione

HRID 1725963Notes

Reaction equation

HRID 1725963 reaction equation
C[O:2][C:3]1[C:8]2[C:9](=[O:14])[O:10][C:11](=[O:13])[NH:12][C:7]=2[CH:6]=[CH:5][CH:4]=1.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl.[Cl-].[Na+].O>[OH:2][C:3]1[C:8]2[C:9](=[O:14])[O:10][C:11](=[O:13])[NH:12][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 107502955-Methoxy-2H-3,1-benzoxazine-2,4(1H)-dione

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A suspension of Example 385A (1.93 g, 10 mmol) in dichloromethane (100 mL) was treated with AlCl3 (2.6 g, 20 mmol), stirred at room temperature overnight, treated slowly with brine (100 mL) while vigorously stirring, and extracted with ethyl acetate. The desired product was obtained as a white solid after evaporation of the solvent. Yield: 1.74 g, 97.2%. 1H NMR (DMSO-d6) δ 6.55 (d, 1H), 6.65 (d, 1H), 7.50 (t, 1H), 10.35 (s, 1H), 11.62 (br s, 1H); MS (ESI(−)) m/e 178 (M−H)−.

Workup

  1. stirringwhile vigorously stirring
  2. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-b7ea625e8b9d4a39a7528e2c8d08c975
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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