N-Methylaniline → HCID 317170, compound

HRID 128829Notes

Reaction equation

[Cl:1][C:2]1[N:3]([CH3:14])[C:4]2[C:9]([C:10]=1[C:11]([OH:13])=O)=[CH:8][CH:7]=[CH:6][CH:5]=2.O=S(Cl)Cl.[CH3:19][NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH3:19][N:20]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:11]([C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]([CH3:14])[C:2]=1[Cl:1])=[O:13]

Participants

Reactant 3

HCID 7515N-Methylaniline

HCID 24386Thionyl Chloride

HCID 995221H-Indole-3-carboxylic acid, 2-chloro-1-methyl-

Product 1

HCID 317170HCID 317170, compoundYield 67%

Procedure

Similar reaction of 2-chloro-1-methylindole-3-carboxylic acid [XXI] with SOCl2 and N-methylaniline gave N-methyl-N-phenyl 2-chloro-1-methylindole-3-carboxamide [XXII: R6 =Me; R7 =Ph] (67% yield); mp (Me2CO/water) 163° C.

Sources & evidence

ORD record: ord-d9c115f2a7c24c609e764cc843cbe50f
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05464861

Reaction notes

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