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

HRID 887907Notes

Reaction equation

HRID 887907 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-5061d1ba66be4b23a26ece03969572b6
Source dataset
uspto-grants-2012_08
Patent number
US08247452B2

Reaction notes

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