2-Bromoethanol → 3-(2-hydroxyethyl)-6,7-dimethoxy-4(3H)-quinazolinone

HRID 858021Notes

Reaction equation

HRID 858021 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][NH:7][C:6]2=[O:15].C1C=CC2N=CN[C:22](=[O:23])[C:20]=2C=1.BrCCO.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[OH:23][CH2:22][CH2:20][N:7]1[C:6](=[O:15])[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8]1

Participants

6

Reactant 4

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 1354087534(1H)-QuinazolinoneHCID 1354950166,7-Dimethoxy-3H-quinazolin-4-one

Product 1

HCID 223266223-(2-hydroxyethyl)-6,7-dimethoxy-4(3H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-(2-hydroxyethyl)-6,7-dimethoxy-4(3H)-quinazolinone was prepared from 6,7-dimethoxy-4(3H)-quinazolinone (3 g, 14.6 mmol). The quinazolinone was combined with 2-bromoethanol (1.14 mL, 16 mmol), an excess of potassium carbonate (10 g) and heated at reflux in 200 mL acetone. The salts were filtered off and the reaction mixture was concentrated. The residue was dissolved in chloroform and washed with water. The organic layer was dried over Na2SO4, filtered and concentrated, 1.39 g (38%); light brown powder; m.p. 130° C., MS: 250.9 (M+H)+

Workup

  1. filtrationThe salts were filtered off
  2. concentrationthe reaction mixture was concentrated
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with water
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e84f45b53fd84f7f8e013a0bad87ffdd
Source dataset
uspto-grants-2006_12
Patent number
US07148235B2

Reaction notes

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