Benzoic acid, 3-methyl-2-nitro-, methyl ester → Methyl 3-methylanthranilate
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[C:3]=1[N+:12]([O-])=O>C(O)(=O)C.O.[Zn]>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[C:3]=1[NH2:12]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
In this example 0.02 mole of 2-methyl-6-methoxycarbonyl-nitrobenzene in 25 ml of acetic acid was added dropwise to a slurry containing 6.5 g of zinc dust suspended in 25 ml of water at 30°-35° C. The resulting exothermic reaction is controlled by maintaining the mixture at about room temperature (about 20°-25° C.) through external cooling. The reaction product mixture was filtered to remove the zinc dust and the filtrate, then washed sequentially with methylene chloride and water, and then extracted with methylene chloride. The extract was washed with an aqueous ammonium hydroxide, then with water and filtered through diatomaceous earth. The filtrate was then dried and evaporated affording 2.7 g of the title product as an oil.
Workup
- customThe resulting exothermic reaction
- temperatureby maintaining the mixture at about room temperature (about 20°-25° C.) through external cooling
- filtrationThe reaction product mixture was filtered
- customto remove the zinc dust
- washthe filtrate, then washed sequentially with methylene chloride and water
- extractionextracted with methylene chloride
- washThe extract was washed with an aqueous ammonium hydroxide
- filtrationwith water and filtered through diatomaceous earth
- customThe filtrate was then dried
- customevaporated
Sources & evidence
- ORD record
- ord-646569bbd62246168bb3550523f026ae
- Source dataset
- uspto-grants-1984_06
- Patent number
- US04456471
Reaction notes
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