Pyridine, 2-[2-(1,1-dimethylethyl)phenoxy]-3-nitro- → 2-(2-Tert-butylphenoxy)pyridin-3-amine

HRID 555391Notes

Reaction equation

HRID 555391 reaction equation
[C:1]([C:5]1[CH:20]=[CH:19][CH:18]=[CH:17][C:6]=1[O:7][C:8]1[C:13]([N+:14]([O-])=O)=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2]>CO.C(OCC)(=O)C.[Pd]>[C:1]([C:5]1[CH:20]=[CH:19][CH:18]=[CH:17][C:6]=1[O:7][C:8]1[C:13]([NH2:14])=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 59857513Pyridine, 2-[2-(1,1-dimethylethyl)phenoxy]-3-nitro-

Product 1

HCID 286054272-(2-Tert-butylphenoxy)pyridin-3-amineYield 112.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1a (7.2 g, 26.5 mmol) was dissolved in a 1:1 mixture of methanol and ethyl acetate (160 mL). Palladium on charcoal (10%, 360 mg, 0.33 mmol) was added, and the mixture was stirred overnight under hydrogen atmosphere. The reaction mixture was filtered over Celite® and concentrated to afford 7.2 g (100%) of 1b as a white powder. [M+H]+=243.3.

Workup

  1. filtrationThe reaction mixture was filtered over Celite®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-6f8f0a853fcc40d696e063e68772e080
Source dataset
uspto-grants-2011_11
Patent number
US08053450B2

Reaction notes

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