HCID 67248293, compound → HCID 67247248, compound

HRID 1422967Notes

Reaction equation

HRID 1422967 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-58354ed3e3b843f3bb7c0a4c584ed6f6
Source dataset
uspto-grants-2015_01
Patent number
US08927541B2

Reaction notes

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