5-Bromo-2-(dimethylamino-methyleneamino)-3-methyl-benzoic acid tert-butyl ester → Tert-butyl 2-amino-5-bromo-3-methylbenzoate
Reaction equation
[C:1]([O:5][C:6](=[O:20])[C:7]1[CH:12]=[C:11]([Br:13])[CH:10]=[C:9]([CH3:14])[C:8]=1[N:15]=CN(C)C)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Cl-].[Zn+2].[Cl-]>[C:1]([O:5][C:6](=[O:20])[C:7]1[CH:12]=[C:11]([Br:13])[CH:10]=[C:9]([CH3:14])[C:8]=1[NH2:15])([CH3:4])([CH3:2])[CH3:3]Participants
4
Procedure
A mixture of 3.52 g (10.3 mmole) of the product of Example 234 and 6.12 g (44.94 mmol) of zinc chloride in 50 ml of absolute ethanol was heated to reflux for 18 hr. The reaction mixture was concentrated in vacuo and the residue was diluted with CH2Cl2 and washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo to provide 2.48 g (84%) of the desired product as a pale brown liquid. Electrospray Mass Spec 286(M+H).