Bromine → 7-Bromo-2-(4-methoxy-phenyl)-6,7-dihydro-5H-quinazolin-8-one

HRID 1175132Notes

Reaction equation

HRID 1175132 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:18]=[CH:17][C:16]3[CH2:15][CH2:14][CH2:13][C:12](=[O:19])[C:11]=3[N:10]=2)=[CH:5][CH:4]=1.[Br:20]Br>Br>[Br:20][CH:13]1[C:12](=[O:19])[C:11]2[N:10]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[N:18]=[CH:17][C:16]=2[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 24408BromineHCID 595585112-(4-Methoxy-phenyl)-6,7-dihydro-5H-quinazolin-8-one

Product 1

HCID 595583987-Bromo-2-(4-methoxy-phenyl)-6,7-dihydro-5H-quinazolin-8-one

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent2×

Procedure

2-(4-Methoxy-phenyl)-6,7-dihydro-5H-quinazolin-8-one (300 mg; 1.2 mmol) in 48% HBr (30 ml) is treated drop-wise with Br2 (189 mg; 1.2 mmol) dissolved in 48% HBr (0.8 ml). The reaction mixture is heated to 350 C for 10 minutes, poured on NaHCO3/water (20 g/100 ml) and extracted with TBME three times. The organic phases are combined, dried over Na2SO4 and evaporated to dryness, yielding the desired product as brown-yellow crystals. 1H-NMR (400 MHz; DMSO-d6): 9.08 (s, 1H); 8.33 (d, 2H); 7.10 (d, 2H); 5.22 (m, 1H); 3.84 (s, 3H); 3.07 (m, 2H); 2.73 (m, 1H); 2.45 (m, 1H). MS (m/z) ES+: 335, 333 (MH+); 255 (80).

Workup

  1. temperatureThe reaction mixture is heated to 350 C for 10 minutes
  2. additionpoured on NaHCO3/water (20 g/100 ml)
  3. extractionextracted with TBME three times
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-d4e1cee329ae4f28b05f414ee8e4a895
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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