p-Toluenesulfonic acid → HCID 178429209, compound

HRID 1762982Notes

Reaction equation

HRID 1762982 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[NH:7][C:6](=[O:12])[C:5]2([CH3:14])[CH3:13].[NH:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[CH:20]=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH3:13][C:5]1([CH3:14])[C:4]2[C:8](=[CH:9][C:10]3[NH:11][C:20]([C:16]4[NH:15][CH:19]=[CH:18][CH:17]=4)=[N:1][C:2]=3[CH:3]=2)[NH:7][C:6]1=[O:12]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 13854Pyrrole-2-carboxaldehydeHCID 135892372H-Indol-2-one, 5,6-diamino-1,3-dihydro-3,3-dimethyl-

Product 1

HCID 178429209HCID 178429209, compound

Procedure

Analogously to Example 2, from 3.8 g. (20 mmol) 5,6-diamino-3,3-dimethylindolin-2-one, 1.9 g. (20 mmol) pyrrole-2-aldehyde and 0.4 g. (2 mmol) p-toluenesulphonic acid, after acidification and evaporation of the reaction mixture, there is obtained the crude product of the title compound. For purification, the residue is worked up with water and the filtrate is neutralised with 2N aqueous ammonia solution and filtered off with suction. The residue is recrystallised from isopropanol with the addition of ethanolic hydrochloric acid. The yield is 1.2 g. (20% of theory); m.p. of the hydrochloride >300° C.

Sources & evidence

ORD record
ord-e9ec615f6c374647b7836ea4ba1d88e5
Source dataset
uspto-grants-1989_05
Patent number
US04835280

Reaction notes

Loading…