HCID 14687427, compound → HCID 59410056, compound

HRID 2404888Notes

Reaction equation

HRID 2404888 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[OH:14])([CH3:3])[CH3:2]>[Pd]>[NH2:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[C:6]([OH:14])[CH:7]=1

Participants

3

Reactant 1

HCID 14687427HCID 14687427, compound

Product 1

HCID 59410056HCID 59410056, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A flask charged with 2-isopropoxy-5-nitro-phenol (100 mg, 0.47 mmol) and palladium on carbon (50 mg, 0.47 mmol) was flushed with N2 followed by evacuating under vacuum. EtOAc (2 mL) and methanol (2 mL) were added under an inert atmosphere followed by evacuating under vacuum. The reaction mixture was then stirred overnight under an atmosphere of hydrogen. The palladium catalyst was removed by filtration and solvent was removed under reduced pressure to give 5-amino-2-isopropoxyphenol (65 mg, 76%). 1H NMR (400.0 MHz, CDCl3) δ 6.73 (d, J=8.3 Hz, 1H), 6.31 (d, J=2.5 Hz, 1H), 6.22 (dd, J=2.5, 8.3 Hz, 1H), 5.22 (s, 1H), 4.50 (qn, J=6.1 Hz, 1H), 3.37 (s, 2H) and 1.37-1.26 (m, 6H) ppm.

Workup

  1. customwas flushed with N2
  2. customby evacuating under vacuum
  3. additionEtOAc (2 mL) and methanol (2 mL) were added under an inert atmosphere
  4. customby evacuating under vacuum
  5. customThe palladium catalyst was removed by filtration and solvent
  6. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-09ce87b76f834225917cd94795ae2ced
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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