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

HRID 468553Notes

Reaction equation

HRID 468553 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-5bdca5023a274858a8ef17713275c87f
Source dataset
uspto-grants-2014_01
Patent number
US08624025B2

Reaction notes

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