HCID 66589491, compound → HCID 18542390, compound

HRID 1880632Notes

Reaction equation

HRID 1880632 reaction equation
[C:1]([Si:5]([CH3:18])([CH3:17])[O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[CH3:16])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[Si:5]([O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[CH3:16])([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:17])[CH3:18]

Participants

5

Reactant 2

HCID 66589491HCID 66589491, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18542390HCID 18542390, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the product from step 1 (3.9 g, 14.6 mmol) and 10% Pd—C (0.5 g, 50% wet) in ethyl acetate was hydrogenated under 50 psi hydrogen for 18 h. The mixture was filtered through Celite and the filtrate was evaporated, providing 3.2 g of 4-(tert-butyldimethylsilyloxy)-3-methylaniline, in 93% yield.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-85ef6043efe44c77a771f39fbeed0f16
Source dataset
uspto-grants-2012_11
Patent number
US08318773B2

Reaction notes

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