5-(Tert-butyl-dimethyl-silanyloxy)-2-nitro-aniline → 4-((tert-Butyldimethylsilyl)oxy)benzene-1,2-diamine

HRID 1696617Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 5-(tert-butyl-dimethyl-silanyloxy)-2-nitro-aniline (1.9 g, 7.08 mmol) in methanol (40 ml) is introduced in a hydrogenation vessel with 10% palladium on carbon catalyst (0.226 g). The reaction mixture is heated at 80° C. for 3 hours under an hydrogen atmosphere (P=1 bar). The reaction mixture is then filtered on Celite® and concentrated under reduced pressure. The residue is dissolved in 10 ml of ethyl acetate and filtered through a silica gel plug (40 ml) that is washed with 600 ml of ethyl acetate. The organic filtrates are concentrated under vacuum to yield 2.55 g of 4-(tert-butyl-dimethyl-silanyloxy)-ortho-phenylenediamine used without further purification in the following step. Analytical LC/MS (method B): retention time=3.12 min., m/z=239.15 (positive ion mode).

Workup

filtrationThe reaction mixture is then filtered on Celite®
concentrationconcentrated under reduced pressure
dissolutionThe residue is dissolved in 10 ml of ethyl acetate
filtrationfiltered through a silica gel plug (40 ml) that
washis washed with 600 ml of ethyl acetate
concentrationThe organic filtrates are concentrated under vacuum

Sources & evidence

ORD record: ord-465a1705c71e49f6ad7c97eeef74e8c6
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163768B2

Reaction notes

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