Ethyl Acetate → HCID 6504213, compound

HRID 571256Notes

Reaction equation

HRID 571256 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]2[N:8]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[C:9](=[O:11])[O:10][C:6]=2[CH:5]=1)([O-])=O.C(OCC)(=O)C>CO.[Pd]>[NH2:1][C:4]1[CH:18]=[CH:17][C:7]2[N:8]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[C:9](=[O:11])[O:10][C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 15258279HCID 15258279, compound

Product 1

HCID 6504213HCID 6504213, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 2-(6-nitro-2-oxobenzo[d]oxazol-3(2H)-yl)acetate (0.570 g, 2.260 mmol) and 10% w/w Pd/C (a catalytic amount) in MeOH (30 ml) and ethyl acetate (30 ml) was hydrogenated in a Parr apparatus at 20 psi for 1 hour. The catalyst was filtered off and the solvent was removed affording methyl 2-(6-amino-2-oxobenzo[d]oxazol-3(2H)-yl)acetate (0.497 g, 2.237 mmol, 99% yield). MS/ESI+ 222.9 [MH]+.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-262dbe969adb4c2fb5c172b767c13b93
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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