3,5-Dimethylaniline → HCID 19780706, compound

HRID 2081814Notes

Reaction equation

HRID 2081814 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[C:8]([CH3:11])[CH:7]=[C:6]([CH3:12])[CH:5]=2.BrC(C)C(OCC)OCC.CC1C=C(C=C(C)C=1)N>>[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][C:6]([CH3:12])=[CH:7][C:8]=2[CH3:11])[NH:3]1

Participants

4

Reactant 3

HCID 79493,5-DimethylanilineHCID 1030012-Bromo-1,1-diethoxypropaneHCID 19780687HCID 19780687, compound

Product 1

HCID 19780706HCID 19780706, compound

Procedure

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.

Workup

  1. customobtained 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)

Sources & evidence

ORD record
ord-93e0d0bc83244103958752a8c9c5ab2e
Source dataset
uspto-grants-1993_02
Patent number
US05185452

Reaction notes

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