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

HRID 892772Notes

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 precipitated 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
customThe white solid which precipitated
filtrationwas filtered off
customdried in vacuo

Sources & evidence

ORD record: ord-13f4aafac68340c4ad9b9607c126bed8
Source dataset: uspto-grants-1992_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05120747

Reaction notes

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