6-Iodoquinazolin-4-one → 4-Hydroxyquinazoline-6-carbonitrile

HRID 2306680Notes

Reaction equation

HRID 2306680 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][NH:6][C:5]2=[O:12].[Cu][C:14]#[N:15]>CN1CCCC1=O>[C:14]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][NH:6][C:5]2=[O:12])#[N:15]

Participants

4

Reactant 2

HCID 1354016666-Iodoquinazolin-4-oneHCID 178418546HCID 178418546, compound

Product 1

HCID 1357038834-Hydroxyquinazoline-6-carbonitrileYield 36.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
170 °C

Procedure

6-Iodoquinazolin-4-one (10 g) in 1-methyl-2-pyrrolidinone (50 ml) was treated with copper (I) cyanide (4.28 g) at 206° C. under N2 for 16 hours. The resulting mixture was cooled to 170° C. and the methyl-2-pyrrolidinone removed by vacuum distillation. Potassium cyanide (2.4 g) in water (30 ml) and ethyl acetate (150 ml) were added to the cooled residue and heating continued at 110° C. for 1.5 hours. This mixture was then filtered hot through a pad of celite and the filter cake washed thoroughly with ethyl acetate. Subsequent separation, drying and concentration in vacuo gave the title compound (2.29 g) as a beige solid; δH [2H6]DMSO 12.65(1H, bs), 8.53(1H, d), 8.28(1H, s), 8.19(1H, dd), 7.82(1H, d); m/z (M−1+) 171.

Workup

  1. customthe methyl-2-pyrrolidinone removed by vacuum distillation
  2. additionPotassium cyanide (2.4 g) in water (30 ml) and ethyl acetate (150 ml) were added to the cooled residue
  3. temperatureheating
  4. filtrationThis mixture was then filtered hot through a pad of celite
  5. washthe filter cake washed thoroughly with ethyl acetate
  6. customSubsequent separation
  7. customdrying
  8. concentrationconcentration in vacuo

Sources & evidence

ORD record
ord-cab593dae11645918d3272f73dc9ea3c
Source dataset
uspto-grants-2004_12
Patent number
US06828320B2

Reaction notes

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