HCID 18184366, compound → HCID 18184387, compound

HRID 1489580Notes

Reaction equation

HRID 1489580 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([N+:13]([O-])=O)[C:10]([OH:16])=[CH:9][C:5]=1[C:6]([NH2:8])=[O:7])([O-])=O>CO.CCOC(C)=O.[Pd]>[NH2:1][C:4]1[CH:12]=[C:11]([NH2:13])[C:10]([OH:16])=[CH:9][C:5]=1[C:6]([NH2:8])=[O:7]

Participants

4

Reactant 1

HCID 18184366HCID 18184366, compound

Product 1

HCID 18184387HCID 18184387, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A solution of 2,4-dinitro-5-hydroxybenzamide (4.00 g, 0.018 mmol) in MeOH/EtOAc (1:1, 50 mL) is hydrogenated over 5% Pd/C at 60 psi for 3 h to give 2,4-diamino-5-hydroxybenzamide, which is used directly. Formic acid (50 mL) is added and the solution is heated under reflux for 48 h. then the volatiles are removed under reduced pressure. The residue is triturated with EtOAc to give crude 4-oxo-3H-oxazolo[5,4-g]quinazoline(3.27 g, 97%) as a tan powder which is used directly.

Sources & evidence

ORD record
ord-f65a16e84abc4c61bd982f254ae3bc70
Source dataset
uspto-grants-1997_10
Patent number
US05679683

Reaction notes

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