Potassium Iodide → 7-Iodoquinazolin-4(3h)-one

HRID 51131Notes

Reaction equation

HRID 51131 reaction equation
N[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.N([O-])=O.[Na+].[I-:17].[K+]>Cl.O>[I:17][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 23668193Sodium NitriteHCID 1354780317-Amino-quinazolin-4-ol

Product 1

HCID 1356162037-Iodoquinazolin-4(3h)-oneYield 17.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

7-Amino-quinazolin-4-one (R. Dempsy and E. Skito, Biochemistry, 30, 1991, 8480) (1.61 g) was suspended in 6N HCl (20 ml) and cooled in an ice bath. A solution of sodium nitrite (0.75 g) in water (10 ml) was added dropwise over 15 minutes. After a further 10 minutes, a solution of potassium iodide (1.66 g) in water (5 ml) was added dropwise. The mixture was warmed to 20° C. and after 3 hours partitioned between ethyl acetate and sodium thiosulphate. The organic phase was dried and concentrated in vacuo to give the title compound (0.485 g); m/z (M+1+) 271.

Workup

  1. temperaturecooled in an ice bath
  2. custompartitioned between ethyl acetate and sodium thiosulphate
  3. customThe organic phase was dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-32f9d0cf1cdf41dc8fc266068a0de7fa
Source dataset
uspto-grants-2004_03
Patent number
US06713485B2

Reaction notes

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