Thionyl Chloride → 5-Methyl-2-methylaminobenzyl chloride hydrochloride
Reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:10][CH3:11])=[C:6]([CH:9]=1)[CH2:7]O.S(Cl)([Cl:14])=O>C1C=CC=CC=1>[ClH:14].[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:10][CH3:11])=[C:6]([CH:9]=1)[CH2:7][Cl:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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).
Sources & evidence
- ORD record
- ord-6ecdfe126d2c4431a16f3f073e779855
- Source dataset
- uspto-grants-1993_01
- Patent number
- US05180836
Reaction notes
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