HCID 18184366, compound → HCID 18184387, compound

HRID 1358263Notes

Reaction equation

HRID 1358263 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-ac7dcea98dc74a988041834a5570fde8
Source dataset
uspto-grants-2003_07
Patent number
US06596726B1

Reaction notes

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