Diisopropylethylamine → 7-fluoro-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 539578Notes

Reaction equation

HRID 539578 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[OH:13])=[O:4].CCN(C(C)C)C(C)C>C(#N)C>[F:12][C:9]1[CH:10]=[CH:11][C:6]2[NH:5][C:3](=[O:4])[CH2:2][O:13][C:7]=2[CH:8]=1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 14998428HCID 14998428, compound

Product 1

HCID 137312957-fluoro-3,4-dihydro-2H-1,4-benzoxazin-3-oneYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-N-(4-fluoro-2-hydroxyphenyl)acetamide (5.5 g, 27 mmol) in acetonitrile (40 mL) was added DIPEA (7 g, 54 mmol) and the reaction solution was stirred at 80° C. for 2 h. The solvent was removed under reduced pressure and the residue was partitioned between dichloromethane (50 mL) and water (50 mL). The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford 3.5 g (78%) of 7-fluoro-2H-benzo[b][1,4]oxazin-3(4H)-one as a brown solid. 1H NMR (400 MHz, CDCl3) δ 8.35 (br. s, 1H) 6.67-6.77 (m, 3H) 4.62 (s, 2H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between dichloromethane (50 mL) and water (50 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-abdbcc7ebd9f49d7829aecb881b8219b
Source dataset
uspto-grants-2014_10
Patent number
US08871754B2

Reaction notes

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