Sodium ethoxide → HCID 178467466, compound

HRID 1443498Notes

Reaction equation

HRID 1443498 reaction equation
Cl[C:2]1[N:11]=[C:10]([OH:12])[C:9]2[C:4](=[C:5]([CH3:15])[C:6]([O:13][CH3:14])=[CH:7][CH:8]=2)[N:3]=1.[CH3:16][CH2:17][O-:18].[Na+]>>[CH2:17]([O:18][C:2]1[N:11]=[C:10]([OH:12])[C:9]2[C:4](=[C:5]([CH3:15])[C:6]([O:13][CH3:14])=[CH:7][CH:8]=2)[N:3]=1)[CH3:16]

Participants

3

Reactant 2

HCID 2723922Sodium ethoxideHCID 1784877522-chloro-7-methoxy-8-methyl-1H-quinazolin-4-one

Product 1

HCID 178467466HCID 178467466, compoundYield 96.6%

Procedure

The quinazolinol (140) (530 mg, 2.36 mmol) was added in small portions to freshly prepared EtONa (740 mg of Na added in 20 mL EtOH). The resulting solution was heated to reflux and after 24 h, the reaction mixture was cooled down to room temperature and evaporated. The residue was re-dissolved in water (10 mL) and the pH of the resulting solution was adjusted to 5 with AcOH. The precipitate was collected by filtration, washed with ice-cooled water and dried to give the title compound (534 mg, 96.6%) as a white solid, m/z=235 (M+H)+.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux and after 24 h
  3. customevaporated
  4. dissolutionThe residue was re-dissolved in water (10 mL)
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with ice-
  7. temperaturecooled water
  8. customdried

Sources & evidence

ORD record
ord-b0960885231f4f5da26cb26d835e2109
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

Loading…