HCID 14091686, compound → HCID 21184834, compound

HRID 1419433Notes

Reaction equation

HRID 1419433 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:12])[CH3:11])=[CH:6][C:5]=1[OH:13])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:11])[CH3:12])=[CH:6][C:5]=1[OH:13]

Participants

4

Reactant 1

HCID 14091686HCID 14091686, compound

Product 1

HCID 21184834HCID 21184834, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-nitro-5-isopropylphenol(1 g, 6.4 mmol) in methanol(50 mL) was added 10% Pd/C (100 mg). The mixture was flushed with argon, then hydrogen was bubbled through the solution for 10 min. and a hydrogen atmosphere was maintained at balloon pressure overnight. The mixture was filtered through celite and the celite was washed with methanol. The solvent was evaporated and chromatography of the resulting solid on silica gel (5% MeOH/CH2Cl2) gave the desired product(775 mg, 93%). 1H NMR (CD3OD): δ 6.71-6.44 (m, 3H), 2.73 (m, 1H), 1.20 (d, 6H).

Workup

  1. customThe mixture was flushed with argon
  2. customhydrogen was bubbled through the solution for 10 min.
  3. temperaturea hydrogen atmosphere was maintained at balloon pressure overnight
  4. filtrationThe mixture was filtered through celite
  5. washthe celite was washed with methanol
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-10cd1f5b28d14e1893dc785142856f50
Source dataset
uspto-grants-1999_03
Patent number
US05886044

Reaction notes

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