Acetic Anhydride → 1-(4-Cyanophenyl)-2,4,6-trimethylimidazo[4,5-c]pyridine

HRID 2107678Notes

Reaction equation

[NH2:1][C:2]1[C:3]([CH3:18])=[N:4][C:5]([CH3:17])=[CH:6][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1.[C:19](OC(=O)C)(=O)[CH3:20]>C(O)(=O)C>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([N:8]2[C:7]3[CH:6]=[C:5]([CH3:17])[N:4]=[C:3]([CH3:18])[C:2]=3[N:1]=[C:19]2[CH3:20])=[CH:10][CH:11]=1)#[N:16]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-amino-4-(4-cyanophenyl)amino-2,6-dimethylpyridine (4.20 g, 17.6 mmol), acetic anhydride (12.6 ml) and acetic acid (12.6 ml) was stirred at 100° C. for 16 hours. The excess of reagents was removed under reduced pressure, and the residual gum was dissolved in water and the solution was rendered basic by the addition of concentrated aqueous ammonia. The white solid which precipitate was filtered off and dried in vacuo to give the title compound (4.06 g, 88%), mp 260°-262° C.

Workup

customThe excess of reagents was removed under reduced pressure
dissolutionthe residual gum was dissolved in water
additionthe solution was rendered basic by the addition of concentrated aqueous ammonia
filtrationThe white solid which precipitate was filtered off
customdried in vacuo

Sources & evidence

ORD record: ord-7a42b42023bc46aa8ea9879c51d211f7
Source dataset: uspto-grants-1990_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04935430

Reaction notes

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