136-90-3,Some common heterocyclic compound, 136-90-3, name is 4-Methoxy-3-methylphenylamine, molecular formula is C8H11NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
EXAMPLE 134 2-[N-(4-Methoxy-3-methylphenyl)-carbamyloxymethyl]-norborn-5-en-2-yl methyl ketone 2.1 g of 80% strength NaH suspension are added to a solution of 10.54 g (0.77 mole) of 4-methoxy-3-methylaniline in 30 ml of THF and the mixture is heated to 40 C. to complete the elimination of hydrogen. When this has ceased, a solution of 20.0 g (0.77 mole) of (2-acetylnorborn-5-en-2-yl)-methyl phenyl carbonate in 20 ml of tetrahydrofuran is added dropwise at room temperature, and the mixture is then stirred for 18 hours at 20 C. After having added a small amount of water, the solvent is stripped off and the residue is taken up in ether. The ether phase is washed repeatedly with 5% strength sodium hydroxide solution, and with water, and is dried over sodium sulfate. The crystalline crude product (11.8 g) is recrystallized from ethyl acetate; 6.4 g of 2-[N-(4-methoxy-3-methylphenyl)-carbamyloxymethyl]-norborn-5-en-2-yl methyl ketone, of melting point 121-122 C., are obtained. Analysis calc. 69.28% C, 7.04% H, 4.25% N, 19.4% O: found 69.4% C, 6.9% H, 4.3% N: C19 H23 NO4 M.Wt. =329.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 136-90-3, its application will become more common.
Reference:
Patent; BASF Aktiengesellschaft; US4335138; (1982); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem