3,5-Dimethylaniline → HCID 19780706, compound

Participants

Reaction Steps

Using a similar procedure to that described in Example 16, 1-acetyl-2,4,6-trimethyl-5-(nitromethylsulphonyl)indoline was obtained in 22% yield as a cream solid, m.p. 175° C.; microanalysis, found: C,51.7; H,5.3; N,8.5%; C14H18N2O5S requires: C,51.5; H,5.6; N,8.6%; NMR (d6 -DMSO): 1.2(3H,d), 2.25(3H,s), 2.4(3H,s), 2.6(3H,s), 2.6-2.8(1H,d), 3.2-3.4(1H,dd), 4.6-4.8(1H,m), 6.4(2H,s), 7.7-8.0(1H,br). The original starting material 2,4,6-trimethylindole, was itself obtained as a yellow oily solid, NMR: 2.39(3H,s), 2.40(3H,s), 2.46(3H,s), 6.15(1H,s), 6.7(1H,s), 6.9(1H,s), 7.6(1H,br) using a similar procedure to that described in J. Org. Chem., 1981, 46(4), 781, starting from 2-bromo-1,1-diethoxypropane and 3,5-dimethylaniline. The intermediate 2,4,6-trimethylindoline was obtained by a similar procedure to that described in connection with 4,6-dimethylindoline in Example 17. It was converted to the corresponding 1-acetyl derivative, m.p. 75° C. without characterisation.

Provenance & Evidence