Acetic Acid → HCID 22349482, compound

HRID 896013Notes

Reaction equation

HRID 896013 reaction equation
[NH2:1][C:2]1[C:7]2[NH:8][CH:9]([CH2:12][OH:13])[CH2:10][O:11][C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:14](O)(=O)[CH3:15]>>[CH3:14][C:15]1[N:8]2[C:7]3[C:6]([O:11][CH2:10][CH:9]2[CH2:12][OH:13])=[CH:5][CH:4]=[CH:3][C:2]=3[N:1]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 22349485(5-Amino-3,4-dihydro-2H-1,4-benzoxazin-3-yl)methanol

Product 1

HCID 22349482HCID 22349482, compound

Conditions

Temperature
95 °C

Procedure

(5-Amino-3,4-dihydro-2H-benzo[1,4]oxazin-3-yl)-methanol (11.8 g, 21.0 mmole) was dissolved in acetic acid (400 mL) and the resulting mixture was stirred at 95° C. overnight. After completion, the reaction was cooled to room temperature and solvent was removed under vacuum and replaced with methanol. Potassium carbonate (2 g) was added and the mixture stirred at room temperature for 1 hour. The solvent was removed and the residue partitioned between 400 mL each of methylene chloride and saturated aqueous sodium bicarbonate. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuum. The crude residue was column chromatographed on silica gel using first methylene chloride to remove impurities and then 5% methanol/methylene chloride to elute 2.34 g of the title compound. 1H NMR (DMSO-d6): δ 7.10 (d, 1H); 7.00 (t, 1H); 6.60 (d, 1H); 5.30 (t, 1H); 4.60 (d, 2H); 4.10 (dd, 1H); 3.60 (m, 2H); 2.50 (s, 3H).

Workup

  1. temperatureAfter completion, the reaction was cooled to room temperature
  2. customsolvent was removed under vacuum
  3. additionPotassium carbonate (2 g) was added
  4. stirringthe mixture stirred at room temperature for 1 hour
  5. customThe solvent was removed
  6. customthe residue partitioned between 400 mL each of methylene chloride and saturated aqueous sodium bicarbonate
  7. washThe organic phase was washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuum
  11. customchromatographed on silica gel using first methylene chloride
  12. customto remove impurities
  13. wash5% methanol/methylene chloride to elute 2.34 g of the title compound

Sources & evidence

ORD record
ord-3f0fc52c75884cdc92b1a4f3f223cec2
Source dataset
uspto-grants-2005_07
Patent number
US06919334B2

Reaction notes

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