Water → 3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrile

HRID 646711Notes

Reaction equation

HRID 646711 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].O.C(=O)(O)[O-].[Na+].Cl[CH2:18][C:19](Cl)=[O:20]>CC(C)=O>[O:20]=[C:19]1[NH:1][C:2]2[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[CH:8][C:9]=2[O:10][CH2:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 2712583-amino-4-hydroxybenzonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 106548133-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
25 °C

Procedure

3-amino-4-hydroxybenzonitrile (g, 10 mmol was dissolved in acetone (20 mL) and water (20 mL) containing sodium bicarbonate (4 g). 2-chloroacetyl chloride was added slowly and the mixture heated to reflux for 4 h and then allowed to stir overnight at 25 ° C. The layers were separated, and the water layer was extracted with ethyl acetate. The organic layers were combined and evaporated to give 3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-carbonitrile as an oil (1.3 g): 1H NMR (400 M ; DMSO-D6): 7.4 (d, 1H); 7.2 (s, 1H); 7.1 (d, 1H).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 4 h
  3. customThe layers were separated
  4. extractionthe water layer was extracted with ethyl acetate
  5. customevaporated

Sources & evidence

ORD record
ord-a10dc335d0274edeba0712d2479874e1
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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