Hydrochloric Acid → 7-methoxy-6-nitroquinazolin-4(3H)-one

HRID 75713Notes

Reaction equation

HRID 75713 reaction equation
F[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[CH3:16][O-:17].[Na+].O([Si](C)(C)C)[K].Cl>CS(C)=O.O>[CH3:16][O:17][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 1353985077-Fluoro-6-nitroquinazolin-4(1H)-oneHCID 178504318HCID 178504318, compound

Product 1

HCID 1355470257-methoxy-6-nitroquinazolin-4(3H)-oneYield 76%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

7-fluoro-6-nitroquinazolin-4(3H)-one (60 g, 287 mmol) in <Step 3> of Example 3 was dissolved in DMSO (600 mL) and sodium methoxide (46.5 g, 861 mmol) was added dropwise thereto in an ice water bath. Thirty minutes later, KOTMS (147 g, 1150 mmol) was added slowly to the water bath, and the mixture was subjected to a reaction for one day. Then, the mixture was neutralized with a 2N HCl solution. Subsequently, the solid thus obtained was filtered and dried to obtain the title compound (48 g, 76%).

Workup

  1. customthe mixture was subjected to a reaction for one day
  2. customSubsequently, the solid thus obtained
  3. filtrationwas filtered
  4. customdried

Sources & evidence

ORD record
ord-967b511c056f4799ad4c91bd56ed6a67
Source dataset
uspto-grants-2014_09
Patent number
US08835458B2

Reaction notes

Loading…