Reaction #6915

ord-5899155eb2234a2e8997519924de4408

Reaction equation

Nc1ccc2c(=O)[nH]cnc2c1
7-Amino-quinazolin-4-one
[I-].[K+]
potassium iodide
O=N[O-].[Na+]
sodium nitrite
→
O=c1[nH]cnc2cc(I)ccc12
title compound
Yield 17.8%
O=c1[nH]cnc2cc(I)ccc12
7-Iodoquinazoline-4-one
Yield 17.8%

Reactants

Nc1ccc2c(=O)[nH]cnc2c1
7-Amino-quinazolin-4-one
[I-].[K+]
potassium iodide
O=N[O-].[Na+]
sodium nitrite

Reagents

None

Solvents

Cl
HCl
O
water
O
water

Conditions

Temperature
20°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturecooled in an ice bath
  2. 2
    Otherpartitioned between ethyl acetate and sodium thiosulphate
  3. 3
    OtherThe organic phase was dried
  4. 4
    Concentrationconcentrated in vacuo

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07084147B2uspto-grants-2006_08