2-Phenylindole → N,N-Dimethylaniline

HRID 1904072Notes

Reaction equation

HRID 1904072 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][C:15]([N:19]([CH3:21])[CH3:20])=[CH:16][CH:17]=3)[C:11](=[O:12])[O:10]2)=[CH:5][CH:4]=1.[C:22]1([C:28]2[NH:29][C:30]3[C:35]([CH:36]=2)=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH2:28]([N:29]([CH2:30][CH3:31])[C:4]1[CH:5]=[C:6]([CH:9]2[C:18]3[C:13](=[CH:14][C:15]([N:19]([CH3:21])[CH3:20])=[CH:16][CH:17]=3)[C:11](=[O:12])[O:10]2)[CH:7]=[CH:8][CH:3]=1)[CH3:22].[CH3:20][N:19]([CH3:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:13][CH:14]=1.[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:36]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[NH:29][C:28]=3[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:18]3[C:13](=[CH:14][C:15]([N:19]([CH3:20])[CH3:21])=[CH:16][CH:17]=3)[C:11](=[O:12])[O:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 136982-PhenylindoleHCID 123896946-(Dimethylamino)-3-(4-methoxyphenyl)-2-benzofuran-1(3H)-one

Product 3

HCID 949N,N-DimethylanilineHCID 12399043HCID 12399043, compoundHCID 204635863-[3-(Diethylamino)phenyl]-6-(dimethylamino)-2-benzofuran-1(3H)-one

Procedure

Example 14 was repeated except that 29 g of 3-(p-methoxyphenyl)-6-dimethylaminophthalide and 19.5 g of 2-phenylindole were used, respectively, instead of 33 g of 3-(m-diethylaminophenyl)-6-dimethylaminophthalide and 13 g of dimethylaniline to obtain 24 g of 3-(p-methoxyphenyl)-3-(2-phenylindole-3-yl)-6-dimethylaminophthalide having the following structure whose m.p. was 224°-225° C. in the form of colourless crystals (Recrystallized from benzene-methanol). This compound becomes blue black on contact with silica gel. ##STR74##

Sources & evidence

ORD record
ord-f7975138868b4344ac766d36552f9488
Source dataset
uspto-grants-1984_03
Patent number
US04439610

Reaction notes

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