Acetic Acid → 7-Amino-6-methoxyquinazoline-2,4(1H,3H)-dione

HRID 855798Notes

Reaction equation

HRID 855798 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[N+:13]([O-])=O)[NH:9][C:8](=[O:16])[NH:7][C:6]2=[O:17].CO.C(O)(=O)C>O1CCCC1.[Pd]>[NH2:13][C:12]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[NH:7][C:8](=[O:16])[NH:9]2)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 688048116-Methoxy-7-nitroquinazoline-2,4(1H,3H)-dione

Product 1

HCID 688051297-Amino-6-methoxyquinazoline-2,4(1H,3H)-dioneYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

120 mg (0.5 mmol) of 6-methoxy-7-nitro-1H-quinazoline-2,4-dione were taken up in a mixture of 5 ml of tetrahydrofuran, 5 ml of methanol and 5 ml of acetic acid and hydrogenated with palladium catalysis at room temperature for 3 hours. The reaction solution was heated to dissolve precipitated product and was filtered hot to remove the catalyst. The filtrate was concentrated and, after addition of toluene, again concentrated. 100 mg (100%) of the desired product were obtained.

Workup

  1. temperatureThe reaction solution was heated
  2. dissolutionto dissolve
  3. customprecipitated product
  4. filtrationwas filtered hot
  5. customto remove the catalyst
  6. concentrationThe filtrate was concentrated
  7. additionafter addition of toluene
  8. concentrationagain concentrated

Sources & evidence

ORD record
ord-6c6314919ca547dcb052a8ffef6ce263
Source dataset
uspto-grants-2007_08
Patent number
US07262220B2

Reaction notes

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