Potassium Carbonate → 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbaldehyde

HRID 566874Notes

Reaction equation

HRID 566874 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[OH:14])[CH:9]=[O:10])=[O:4].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[O:4]=[C:3]1[NH:5][C:6]2[CH:7]=[C:8]([CH:9]=[O:10])[CH:11]=[CH:12][C:13]=2[O:14][CH2:2]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 212639083-(Chloroacetylamino)-4-hydroxy-benzaldehyde

Product 1

HCID 107736383-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbaldehydeYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(Chloroacetylamino)-4-hydroxy-benzaldehyde (2.4 g, 13.2 mmol) and potassium carbonate (9.1 g, 66.1 mmol) are stirred at room temperature in 50 mL of acetonitrile for 12 hours. The acetonitrile is evaporated and the residue is taken up in 50 mL of water. After standing at room temperature for 10 minutes, the precipitate is collected by filtration and recrystallized from ethyl acetate to give 1.4 g (60% yield) of 3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbaldehyde; mp 220-222° C.

Workup

  1. customThe acetonitrile is evaporated
  2. filtrationthe precipitate is collected by filtration
  3. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-7b53db98cf2f441ba191a2e606e1983f
Source dataset
uspto-grants-2001_01
Patent number
US06177422B1

Reaction notes

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