Propargyl bromide → 1-(2-propynyl)1H-imidazo[4,5-c]quinolin-4-amine

Reaction equation

[NH:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[C:5]([NH2:14])[C:4]=2[N:3]=[CH:2]1.[CH2:15](Br)[C:16]#[CH:17]>>[CH2:17]([N:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[C:5]([NH2:14])[C:4]=2[N:3]=[CH:2]1)[C:16]#[CH:15]

Participants

Reactant 2

HCID 7842Propargyl bromide

HCID 178508172HCID 178508172, compound

Product 1

HCID 152228081-(2-propynyl)1H-imidazo[4,5-c]quinolin-4-amineYield 15.8%

Procedure

Using the general method of Example 1, 2.1 g of 1H-imidazo[4,5-c]quinolin-4-amine was reacted with 1.7 g of propargyl bromide to provide 0.4 g of 1-(2-propynyl)-1H-imidazo[4,5-c]quinolin-4-amine, m.p. 220°-222° C. The structure was confirmed by nuclear magnetic resonance spectroscopy. Analysis: Calculated for C13H10N4 : %C, 70.3; %H, 4.5; %N, 25.2; Found: %C, 70.5; %H, 4.6; %N, 25.4.

Sources & evidence

ORD record: ord-f4e901de007d4123a7f01c90712f0f48
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05714608

Reaction notes

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