Tert-butyl(5-methoxy-2-nitrobenzyloxy)dimethylsilane → 2-((Tert-butyldimethylsilyloxy)methyl)-4-methoxyaniline

HRID 1627684Notes

Reaction equation

[C:1]([Si:5]([O:8][CH2:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[N+:18]([O-])=O)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[Si:5]([O:8][CH2:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[NH2:18])([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:6])[CH3:7]

Participants

Conditions

Temperature: 30 °C

Procedure

To a solution of tert-butyl(5-methoxy-2-nitrobenzyloxy)dimethylsilane (14.0 g, 47.1 mmol) in EtOH (200 mL) was added 10% Pd/C (1.40 g), the mixture was stirred at 30° C. for 2 hours under H2 (40 psi). The solids were filtered off and the filtrate was concentrated under reduced pressure to give the product (14.0 g) as a yellow oil. 1H NMR (DMSO 400 MHz): δ 6.75 (d, J=2.4 Hz, 1H), 6.60-6.55 (m, 2H), 4.55 (s, 2H), 4.40 (brs, 2H), 3.61 (s, 3H), 0.90 (s, 9H), 0.09 (s, 6H).

Workup

filtrationThe solids were filtered off
concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-1ed04aa343e445979516f62439361b09
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785643B2

Reaction notes

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