HCID 67248293, compound → HCID 67247248, compound

HRID 2273256Notes

Reaction equation

HRID 2273256 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][C:11]1[O:10][CH2:9][C:8]([C:17]([OH:19])=[O:18])=[CH:7][C:6]2=1>[Pd].CO.O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][C:11]1[O:10][CH2:9][CH:8]([C:17]([OH:19])=[O:18])[CH2:7][C:6]2=1

Participants

5

Reactant 1

HCID 67248293HCID 67248293, compound

Product 1

HCID 67247248HCID 67247248, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

10% Palladium on activated carbon (140 mg, 0.14 mmol, 0.05 eq) is added at room temperature to a stirred solution of 6-methoxy-2H-1-oxa-9-aza-phenanthrene-3-carboxylic acid (700 mg, 2.72 mmol, 1.0 eq) in methanol (20 mL) and tetrahydrofuran (20 mL). The resulting mixture is stirred under hydrogen flow (3 bars) at room temperature for 48 hours. The catalyst is then removed by filtration and the solution is concentrated to afford 6-methoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthrene-3-carboxylic acid as a light yellow semisolid (520 mg, 74% yield) which is directly engaged in the next step.

Workup

  1. customThe catalyst is then removed by filtration
  2. concentrationthe solution is concentrated

Sources & evidence

ORD record
ord-46f45c9d1b2f4d03b976f68661ddcddc
Source dataset
uspto-grants-2015_09
Patent number
US09120822B2

Reaction notes

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