2,5-Dimethoxybenzonitrile → 2,5-Dimethoxybenzenemethanamine

HRID 1037665Notes

Reaction equation

HRID 1037665 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[O:11][CH3:12])#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:2][CH2:1][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[O:11][CH3:12]

Participants

4

Reactant 2

HCID 792002,5-DimethoxybenzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 186522,5-DimethoxybenzenemethanamineYield 93.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A sample of 3.12 g of 2-cyano-1,4-dimethoxybenzene was reduced by 1 g of lithium aluminum hydride in 20 mL of THF at 0° C. to yield 3 g of 2-aminomethyl-1,4-dimethoxybenzene. This was then refluxed in a 1:1 (v/v) mixture of acetic acid and 48% aqueous hydrobromic acid overnight. The volatile components were removed under reduced pressure, and the crude 2-aminomethyl-1,4-hydroquinone HBr salt was used “as is” without further purification. Triethylamine (0.4 mL) was added to a mixture of 50 mg of compound (1) and 0.6 mmole of 2-aminomethyl-1,4-dihydroquinone HBr salt in 2 mL of dichloroethane, and stirred overnight. The crude dihydroquinone was then oxidized to the desired quinone compound (11) with ceric ammonium nitrate in a water/acetonitrile mixture.

Sources & evidence

ORD record
ord-b652b63011e14d95ac5627690180c2dc
Source dataset
uspto-grants-2013_10
Patent number
US08546580B2

Reaction notes

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