Lithium iodide → 3-(4,4-Dimethyl-8-hydroxy-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-5-fluorobenzonitrile

HRID 413182Notes

Reaction equation

HRID 413182 reaction equation
[CH3:1][C:2]1([CH3:24])[C:7]2[CH:8]=[C:9]([C:14]3[CH:15]=[C:16]([CH:19]=[C:20]([F:22])[CH:21]=3)[C:17]#[N:18])[CH:10]=[C:11]([O:12]C)[C:6]=2[NH:5][C:4](=[O:23])[O:3]1.[I-].[Li+]>N1C(C)=CC(C)=CC=1C>[CH3:1][C:2]1([CH3:24])[C:7]2[CH:8]=[C:9]([C:14]3[CH:15]=[C:16]([CH:19]=[C:20]([F:22])[CH:21]=3)[C:17]#[N:18])[CH:10]=[C:11]([OH:12])[C:6]=2[NH:5][C:4](=[O:23])[O:3]1

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 235096143-(4,4-dimethyl-8-methoxy-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-5-fluorobenzonitrile

Product 1

HCID 235096263-(4,4-Dimethyl-8-hydroxy-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-5-fluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

A mixture of 3-(4,4-dimethyl-8-methoxy-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-5-fluorobenzonitrile (0.1 g, 0.31 mmol), Lithium iodide (0.3 g, 2.24 mmol) in 2,4,6-collidine was heated at reflux under nitrogen for 5 hours. The solvent was removed in vacuo and the residue was taken in a mixture of brine (10 mL) and ethyl acetate (30 mL). The organic layer was separated, dried (MgSO4), and evaporated. The resultant residue was purified on a silica gel column chromatography (hexane:ethyl acetate/1:1) to give the title compound as white plates (0.03 mg, 31%): mp 197-198° C.; 1H-NMR (DMSO-d6) δ10.16 (s, 1H), 9.55 (s, 1H), 8.01 (s, 1H), 7.79-7.87 (m, 2H), 7.20 (s,1H), 7.08 (d, 1H, J=1.0 Hz), 1.65 (s, 6H). MS (ESI) m/z 311 [M−H]−.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 5 hours
  3. customThe solvent was removed in vacuo
  4. additionthe residue was taken in a mixture of brine (10 mL) and ethyl acetate (30 mL)
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe resultant residue was purified on a silica gel column chromatography (hexane:ethyl acetate/1:1)

Sources & evidence

ORD record
ord-e0b47be504864cf5b6d67548827904f9
Source dataset
uspto-grants-2003_05
Patent number
US06566358B2

Reaction notes

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