4-Nitro-m-toluidine → HCID 21956270, compound

HRID 840862Notes

Reaction equation

HRID 840862 reaction equation
[CH3:1]C1C=C(C=CC=1[N+]([O-])=O)N.[CH3:12][C:13]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18]2[C:14]=1[C:15](=[O:26])[C:16](=[O:25])[NH:17]2.[CH:27]1[C:32]([NH:33][NH2:34])=[CH:31][CH:30]=[C:29]([S:35]([NH2:38])(=[O:37])=[O:36])[CH:28]=1.Cl>>[CH3:12][C:13]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18]2[C:14]=1[C:15](=[O:26])[C:16](=[O:25])[NH:17]2.[CH3:1][NH:38][S:35]([C:29]1[CH:28]=[CH:27][C:32]([NH:33][N:34]=[C:15]2[C:14]3[C:18](=[CH:19][CH:20]=[C:21]([N+:22]([O-:24])=[O:23])[C:13]=3[CH3:12])[NH:17][C:16]2=[O:25])=[CH:31][CH:30]=1)(=[O:36])=[O:37]

Participants

5

Reactant 3

HCID 118984-Nitro-m-toluidineHCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 21956270HCID 21956270, compound

Product 2

HCID 21956270HCID 21956270, compoundHCID 178486275HCID 178486275, compound

Procedure

4-Methyl-5-nitro-1H-indole-2,3-dione was prepared from 3-methyl-4-nitroaniline according to Procedure A: 1H NMR (DMSO-d6): δ11.5 (s, 1H), 8.2 (d, 1H), 6.8 (d, 1H), 2.7 (s, 3H); APCI−MS m/z 205 (M−H)−. The title compound was prepared in 84% yield from 4-methyl-5-nitro-1H-indole-2,3-dione and 4-sulfonamidophenylhydrazine hydrochloride according to Procedure G: 1H NMR (DMSO-d6): δ13.0 (s, 1H), 11.6 (s, 1H), 7.9 (d,1H), 7.7 (d, 2H), 7.6 (d, 2H), 7.3 (q, 1H), 6.9 (d, 1H), 2.8 (s, 3H), 2.4 (d, 3H); APCI−MS m/z 388 (M−H)−.

Sources & evidence

ORD record
ord-d3b37261b24c46bf968cc3bf84c1186b
Source dataset
uspto-grants-2002_04
Patent number
US06369086B1

Reaction notes

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