Acetic Acid → 2,7-dimethyl-1H-imidazo(4,5-b)pyridine

HRID 1029566Notes

Reaction equation

HRID 1029566 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([CH3:9])[CH:5]=[CH:4][N:3]=1.[C:10](O)(=O)[CH3:11]>>[CH3:10][C:11]1[NH:8][C:7]2[C:2]([N:1]=1)=[N:3][CH:4]=[CH:5][C:6]=2[CH3:9]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 3174954-Methylpyridine-2,3-diamine

Product 1

HCID 223885532,7-dimethyl-1H-imidazo(4,5-b)pyridine

Procedure

The title compound was prepared from 2,3-diamino-4-picoline (0.246 g, 2 mmol) and acetic acid (0.15 ml) according to the procedure described in Step 1 of Example 9. The crude product was purified by flash chromatography on silica-gel using EtOAc-MeOH (9:1) to give the pure product (0.25 g, 85%) as a light brown solid. 1H NMR (300 MHz, CDCl3): 8.14 (d, 1H, J=5 Hz), 7.01 (d, 1H, J=5 Hz), 2.73 (s, 3H), 2.62 (s, 3H).

Workup

  1. customThe crude product was purified by flash chromatography on silica-gel

Sources & evidence

ORD record
ord-b5519e2c15a448af9532b5ac23d729d0
Source dataset
uspto-grants-1992_04
Patent number
US05102880

Reaction notes

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