Aniline → HCID 178526540, compound

HRID 2218418Notes

Reaction equation

HRID 2218418 reaction equation
[Cl:1][C:2]1[C:3](Cl)=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1.[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>ClC1C=CC=CC=1Cl.CO>[Cl:1][C:2]1[C:3]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 8857Ethyl AcetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 178526538HCID 178526538, compound

Product 1

HCID 178526540HCID 178526540, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
180 °C

Procedure

6,7-Dichloro-2-(4-nitrophenyl)-3H-imidazo[4,5-b]pyridine (0.73 g, 2.4 mmol), aniline (0.70 ml) and a catalytical amount of p-toluenesulfonic acid monohydrate were dissolved in o-dichlorobenzene (4.0 ml) and heated to 180° C. for 5 h. Ethyl acetate and methanol were added, the mixture stirred and the solid filtered off to afford the title compound (0.68 g, 77%).

Workup

  1. filtrationthe solid filtered off

Sources & evidence

ORD record
ord-f18c32479bd648faae9fcfa565ecfd20
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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