Potassium Chloride → 3,4-dihydro-2H-1,4-benzoxazine-2-carbonitrile

HRID 1483029Notes

Reaction equation

HRID 1483029 reaction equation
Cl[C:2](=[CH2:5])[C:3]#[N:4].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13].[Cl-].[K+]>CC(C)=O>[O:13]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][CH2:5][CH:2]1[C:3]#[N:4]

Participants

5

Reactant 3

HCID 4873Potassium ChlorideHCID 58012-AminophenolHCID 701982-Chloroacrylonitrile

Product 1

HCID 27955043,4-dihydro-2H-1,4-benzoxazine-2-carbonitrileYield 31.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Combine 2-chloro-2-propenenitrile (3.0 g, 34.3 mmol), 2-aminophenol (3.27 g, 29.96 mmol), acetone (50 mL), and potassium chloride (5 g, 36.18 mmol). Stir the mixture at ambient temperature for 16 hours. Filter the mixture and wash the filter cake with EtOAc. Concentrate the filtrate under reduced pressure to give a residue. Purify via flash column chromatography using a gradient of 1-50% EtOAc in petroleum ether to elute. Combine the product fractions and remove solvents under reduced pressure to provide the title compound (1.5 g, 21.6%). MS (m/z): 161 (M+1).

Workup

  1. filtrationFilter the mixture
  2. washwash the filter cake with EtOAc
  3. concentrationConcentrate the filtrate under reduced pressure
  4. customto give a residue
  5. customPurify via flash column chromatography
  6. washto elute
  7. customCombine the product fractions and remove solvents under reduced pressure

Sources & evidence

ORD record
ord-bd0f5f84560741e393df1207e8f4711f
Source dataset
uspto-grants-2016_08
Patent number
US09416138B2

Reaction notes

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