HCID 18184366, compound → HCID 18184387, compound

HRID 1249738Notes

Reaction equation

HRID 1249738 reaction equation
O=C1C2N=CN=CC=2C=C2OCNC12.[OH:15][C:16]1[C:17]([N+:28]([O-])=O)=[CH:18][C:19]([N+:25]([O-])=O)=[C:20]([CH:24]=1)[C:21]([NH2:23])=[O:22]>[Pd]>[NH2:25][C:19]1[CH:18]=[C:17]([NH2:28])[C:16]([OH:15])=[CH:24][C:20]=1[C:21]([NH2:23])=[O:22]

Participants

4

Reactant 2

HCID 18184366HCID 18184366, compoundHCID 69704031HCID 69704031, compound

Product 1

HCID 18184387HCID 18184387, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Scheme 2 can be illustrated with reference to the preparation of 4-oxo-3H-oxazolo[5,4-g]quinazoline. In this process, 5-hydroxy-2,4-dinitrobenzamide (compound of formula VIII in which Y1 is amino, Y2 is O, Y4 is hydroxy and Y5 is nitro) is hydrogenated over 5% palladium over carbon at about 60 psi for about 3 hours to give 2,4-diamino-5-hydroxybenzamide. To this product is added formic acid and the mixture is heated to reflux for about 48 hours to provide 4-oxo-3H-oxazolo[5,4-g]quinazoline. In this process, steps 1 and 2 of Scheme 2 are performed as a single step.

Sources & evidence

ORD record
ord-f7ceae22eb8049af87fe7113330ab547
Source dataset
uspto-grants-2002_01
Patent number
US06335344B1

Reaction notes

Loading…