2-Methylindole → N,N-Dimethylaniline

HRID 325994Notes

Reaction equation

HRID 325994 reaction equation
CO[C:3]1[CH:8]=[C:7](OC)[CH:6]=[CH:5][C:4]=1[CH:11]1[C:20]2[C:15](=[CH:16][C:17]([N:21]([CH3:23])[CH3:22])=[CH:18][CH:19]=2)[C:13](=[O:14])[O:12]1.C[C:25]1[NH:26][C:27]2C(C=1)=CC=CC=2>>[CH3:25][N:26]([CH3:27])[C:7]1[CH:6]=[CH:5][C:4]([CH:11]2[C:20]3[C:15](=[CH:16][C:17]([N:21]([CH3:23])[CH3:22])=[CH:18][CH:19]=3)[C:13](=[O:14])[O:12]2)=[CH:3][CH:8]=1.[CH3:22][N:21]([CH3:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 72242-MethylindoleHCID 123990273-(2,4-dimethoxyphenyl)-6-(dimethylamino)isobenzofuran-1(3H)-one

Product 2

HCID 949N,N-DimethylanilineHCID 936931(3H)-Isobenzofuranone, 6-(dimethylamino)-3-[4-(dimethylamino)phenyl]-

Procedure

Example 1 was repeated except that 32 g of 3-(2',4'-dimethoxyphenyl)-6-dimethylaminophthalide and 13.5 g of 2-methylindole were used, respectively, instead of 30 g of 3-(p-dimethylaminophenyl)-6-dimethylaminophthalide and 13 g of dimethylaniline to obtain 27 g of triarylmethane having the following structure whose m.p. was 202°-203° C. in the form of colourless crystals (Recrystallized from methanol). This compound becomes bluish violet upon exposure to light on silica gel. ##STR13##

Sources & evidence

ORD record
ord-40a44664462543cbb4bf87231e55f95b
Source dataset
uspto-grants-1984_04
Patent number
US04443614

Reaction notes

Loading…