Aniline → HCID 178478243, compound

HRID 868502Notes

Reaction equation

HRID 868502 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[N:10][C:5]2=[C:4](Cl)[CH:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CO>[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[N:10][C:5]2=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 1784781755,7-dichloro-4H-imidazo[4,5-b]pyridine

Product 1

HCID 178478243HCID 178478243, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5,7-Dichloro-3H-imidazo[4,5-b]pyridine (4.4 g, 23.3 mMol) was heated with 50 mL of aniline at 135° C. under a nitrogen atmosphere. After 48 hours the reaction mixture was cooled and diluted with 50 mL methanol. The 5-chloro-7-anilino-3H-imidazo[4,5-b]pyridine was isolated and washed with methanol. The dried solid weighed 4.8 g. Yield 19.6 mMol, 84%; m.p. >300° C.; NMR (DMSO-d6): 9.23 δ (s, 1H, NH-anilino); 8.24 (s, 1H, H2); 7.44-7.37 (m, 5H, aromatic); 6.69 (s, 1H, H5).

Workup

  1. temperatureAfter 48 hours the reaction mixture was cooled

Sources & evidence

ORD record
ord-84299e9801a24153b2b89e7e3c01d8cc
Source dataset
uspto-grants-1988_10
Patent number
US04780452

Reaction notes

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