7-Nitroquinazolin-4(3H)-one → 7-Amino-quinazolin-4-ol

HRID 1171626Notes

Reaction equation

HRID 1171626 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([C:8](=[O:14])[NH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([C:8](=[O:14])[NH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 862228007-Nitroquinazolin-4(3H)-one

Product 1

HCID 1354780317-Amino-quinazolin-4-olYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd/C (100 mg) was added as a single portion to a degassed and flushed (3×Ar) suspension of 7-nitroquinazolin-4-one (1.15 g, 6.02 mmol) in methanol (150 mL). The resulting black mixture was degassed, flushed with hydrogen and allowed to stir for 4 hours. The mixture was filtered through celite, washed well with methanol, and the filtrate concentrated to give a tanned solid. This was purified by column chromatography (silica) using 10% methanol/ethyl acetate as the eluent. Combined fractions gave a beige solid (949 mg, 98% yield).

Workup

  1. customa degassed
  2. customflushed
  3. customThe resulting black mixture was degassed
  4. customflushed with hydrogen
  5. filtrationThe mixture was filtered through celite
  6. washwashed well with methanol
  7. concentrationthe filtrate concentrated
  8. customto give a tanned solid
  9. customThis was purified by column chromatography (silica)

Sources & evidence

ORD record
ord-a42160a15cc94fbfaf3e0d75f6cfc6d3
Source dataset
uspto-grants-2010_11
Patent number
US07829705B2

Reaction notes

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