HCID 58043648, compound → HCID 58044268, compound

HRID 1918995Notes

Reaction equation

HRID 1918995 reaction equation
[CH3:1][C:2]1([OH:15])[CH2:5][N:4]([C:6]2[CH:7]=[N:8][C:9]([N+:12]([O-])=O)=[CH:10][CH:11]=2)[CH2:3]1>[Pd].CO>[NH2:12][C:9]1[N:8]=[CH:7][C:6]([N:4]2[CH2:5][C:2]([CH3:1])([OH:15])[CH2:3]2)=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 58043648HCID 58043648, compound

Product 1

HCID 58044268HCID 58044268, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 100-mL Parr hydrogenation bottle was purged with nitrogen and charged with 207a (2.3 g, 11 mmol), 10% palladium on carbon (50% wet, 1.0 g) and methanol (100 mL). The bottle was evacuated, charged with hydrogen gas to a pressure of 25 psi and shaken for 2 h on a Parr hydrogenation apparatus. The hydrogen was then evacuated and nitrogen charged to the bottle. The catalyst was removed by filtration through a pad of Celite and the filtrate was concentrated under reduced pressure to afford 207b (1.85 g, 92%). MS: [M+H]+ 180.

Workup

  1. customA 100-mL Parr hydrogenation bottle was purged with nitrogen
  2. customThe bottle was evacuated
  3. additioncharged with hydrogen gas to a pressure of 25 psi
  4. customThe hydrogen was then evacuated
  5. additionnitrogen charged to the bottle
  6. customThe catalyst was removed by filtration through a pad of Celite
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0c1e39ca729045fd972b9bd44a6c7dac
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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