Chlorotrimethylsilane → 2-(3-Methylphenyl)ethan-1-amine

HRID 1844022Notes

Reaction equation

HRID 1844022 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](/[CH:8]=[CH:9]/[N+:10]([O-])=O)[CH:3]=1.[Li+].[BH4-].C[Si](Cl)(C)C>C1COCC1>[C:2]1([CH3:1])[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][NH2:10])[CH:3]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 4148881Lithium borohydrideHCID 12623346HCID 12623346, compound

Product 1

HCID 4100852-(3-Methylphenyl)ethan-1-amineYield 200.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-1-Methyl-3-(2-nitrovinyl)benzene (9 g, 55.214 mmol) was reacted with LiBH4 (4.81 g, 2220.85 mmol), trimethylsilyl chloride (55.86 mL, 441.7 mmol) and dry THF (120 mL) to afford 15 g of the crude product.

Sources & evidence

ORD record
ord-10e4b7668fe9409084aa6c57da1061ab
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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