Iodide Ion → 1H-imidazo[4,5-c]quinolin-1-yl ether

HRID 431592Notes

Reaction equation

HRID 431592 reaction equation
[N:1]1([OH:14])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.[I-]>>[N:1]1([O:14][N:1]2[C:13]3[C:12]4[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=4[N:6]=[CH:5][C:4]=3[N:3]=[CH:2]2)[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1

Participants

3

Reactant 2

HCID 30165Iodide IonHCID 666208601H-imidazo[4,5-c]quinolin-1-ol

Product 1

HCID 218980241H-imidazo[4,5-c]quinolin-1-yl ether

Procedure

In step (3) of Reaction Scheme II a 1H-imidazo[4,5-c]quinolin-1-yl alcohol of Formula X is alkylated with an iodide of Formula XVII to provide a 1H-imidazo[4,5-c]quinolin-1-yl ether of Formula XVIII. The alcohol of Formula X is reacted with sodium hydride in a suitable solvent such as N,N-dimethylformamide to form an alkoxide. The iodide is added to the alkoxide solution at ambient temperature. After the addition is complete the reaction is stirred at an elevated temperature (˜100° C.).

Sources & evidence

ORD record
ord-c54f232805f340c8aacf5052bc7e576e
Source dataset
uspto-grants-2003_12
Patent number
US06660747B2

Reaction notes

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