Sodium Hydroxide → 2-chloro-7-methoxy-8-methyl-1H-quinazolin-4-one

HRID 1443490Notes

Reaction equation

HRID 1443490 reaction equation
[OH-:1].[Na+].[Cl:3][C:4]1[N:13]=[C:12](Cl)[C:11]2[C:6](=[C:7]([CH3:17])[C:8]([O:15][CH3:16])=[CH:9][CH:10]=2)[N:5]=1>O.C1COCC1>[Cl:3][C:4]1[N:13]=[C:12]([OH:1])[C:11]2[C:6](=[C:7]([CH3:17])[C:8]([O:15][CH3:16])=[CH:9][CH:10]=2)[N:5]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 591654322,4-Dichloro-7-methoxy-8-methylquinazoline

Product 1

HCID 1784877522-chloro-7-methoxy-8-methyl-1H-quinazolin-4-oneYield 99.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A solution of NaOH (1.58 g, 39.6 mmol) in water (40 mL) was added to 2,4-dichloro-7-methoxy-8-methylquinazoline (139) (3.2 g, 13.05 mmol) in THF (20 mL). The resulting mixture was heated at 40° C. for 24 h. Then, the reaction mixture was cooled to room temperature, THF was evaporated and additional water (30 mL) was added. The precipitate was filtered off. Then, the pH of the filtrate was adjusted to 5 with AcOH to give a solid which was subsequently filtered off and successively washed with water and isopropylether to give the title compound (2.91 g, 99%) as a yellowish powder: m/z=225 (M+H)+.

Workup

  1. temperatureThen, the reaction mixture was cooled to room temperature
  2. customTHF was evaporated
  3. additionadditional water (30 mL) was added
  4. filtrationThe precipitate was filtered off
  5. customto give a solid which
  6. filtrationwas subsequently filtered off
  7. washsuccessively washed with water and isopropylether

Sources & evidence

ORD record
ord-3ebf83711de04fe6829a5b30fbc2ae75
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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