Sodium periodate → 3-(2-Chlorophenyl)-6-fluoro-3,4-dihydroquinazolin-4-one-2-carboxaldehyde

HRID 1169275Notes

Reaction equation

HRID 1169275 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([F:25])[CH:21]=2)[N:16]=[C:15]1[CH:26]=CN(C)C>O1CCCC1>[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([F:25])[CH:21]=2)[N:16]=[C:15]1[CH:26]=[O:2]

Participants

4

Reactant 2

HCID 23667635Sodium periodateHCID 540627153-(2-Chloro-phenyl)-6-fluoro-2-(2-dimethylamino-vinyl)-3,4-dihydro-quinazolin-4-one

Product 1

HCID 106858093-(2-Chlorophenyl)-6-fluoro-3,4-dihydroquinazolin-4-one-2-carboxaldehydeYield 101.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a well stirred mixture of sodium periodate (2.24 g, 10.47 mmol) in pH 7 buffer (10 mL) and tetrahydrofuran (10 mL) was added 3-(2-chloro-phenyl)-6-fluoro-2-(2-dimethylamino-vinyl)-3,4-dihydro-quinazolin-4-one (0.90 g, 2.62 mmol) all at once. The mixture warmed slightly to the touch and was stirred 1 h at ambient temperature. The reaction was filtered through celite and the pad was rinsed with ethyl acetate. The phases were separated from the filtrate and the aqueous layer was extracted with ethyl acetate. The combined organic phase was washed with brine, dried over magnesium sulfate, and concentrated to afford 0.802 g (97%) of 3-(2-chloro-phenyl)-6-fluoro-3,4-dihydro-quinazolin-4-one-2-carboxaldehyde as a 1:2 mixture of free aldehyde and hydrate which had: 1H NMR δ 9.52 (s,) [CHO], 8.20-7.45 (m, 7H), 6.75 (d, J=7.4 Hz) [hydrate OH] and 6.49 (d, J=8 Hz) [hydrate OH], 5.14 (t, J=7.5 Hz) [hydrate methine CH].

Workup

  1. temperatureThe mixture warmed slightly to the touch
  2. stirringwas stirred 1 h at ambient temperature
  3. filtrationThe reaction was filtered through celite
  4. washthe pad was rinsed with ethyl acetate
  5. customThe phases were separated from the filtrate
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. washThe combined organic phase was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-504f42d105d14b87914eb342b9b9dc6f
Source dataset
uspto-grants-2003_09
Patent number
US06627755B1

Reaction notes

Loading…