2-Methylindole → N,N-Dimethylaniline

HRID 325993Notes

Reaction equation

HRID 325993 reaction equation
CO[C:3]1[CH:4]=[C:5]([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:6]=[CH:7][C:8]=1OC.C[C:25]1[NH:26][C:27]2C(C=1)=CC=CC=2>>[CH3:25][N:26]([CH3:27])[C:8]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=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 123896963-(3,4-Dimethoxyphenyl)-6-(dimethylamino)-2-benzofuran-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-(3',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 33 g of triarylmethane having the following structure whose m.p. was 230°-232° C. in the form of colourless crystals (Recrystallized from methanol). This compound becomes bluish violet upon exposure to light on silica gel. ##STR11##

Sources & evidence

ORD record
ord-c62daddeee1144caa77b77bc779e1675
Source dataset
uspto-grants-1984_04
Patent number
US04443614

Reaction notes

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