Dimethyl Sulfate → 5-Methyl-2-methylaminobenzyl alcohol

HRID 1646701Notes

Reaction equation

HRID 1646701 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:3]=1[C:4](OCC)=[O:5].[CH3:14]OS(=O)(=O)OC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH3:13][C:10]1[CH:11]=[CH:12][C:2]([NH:1][CH3:14])=[C:3]([CH:9]=1)[CH2:4][OH:5]

Participants

4

Reactant 3

HCID 6497Dimethyl SulfateHCID 12327280Ethyl 2-amino-5-methylbenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 544746825-Methyl-2-methylaminobenzyl alcohol

Procedure

Ethyl 2-amino-5-methylbenzoate was treated with dimethylsulfuric acid to give a N-methylated product. The N-methylated product was reduced using lithium aluminum hydride to give 5-methyl-2-methylaminobenzyl alcohol. The obtained alcohol was reacted with thionyl chloride in benzene to give the desired compound, yield 22% (based on the amount of the starting benzoate).

Workup

  1. customto give a N-methylated product

Sources & evidence

ORD record
ord-e3702e88520244688c7e60a0e1a1e3c8
Source dataset
uspto-grants-1993_01
Patent number
US05180836

Reaction notes

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