Triethylamine → 4-chloro-2-(ethoxymethyl)-1-prop-2-ynyl-1H-imidazo[4,5-c]quinoline

HRID 606041Notes

Reaction equation

[Cl:1][C:2]1[C:11]([NH:12][C:13](=O)[CH2:14][O:15][CH2:16][CH3:17])=[C:10]([NH:19][CH2:20][C:21]#[CH:22])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C>C(O)C>[Cl:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:14][O:15][CH2:16][CH3:17])[N:19]([CH2:20][C:21]#[CH:22])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of N-[2-chloro-4-(prop-2-ynylamino)quinolin-3-yl]-2-ethoxyacetamide (26.7 g, 84.0 mmol) and triethylamine (17.5 mL, 126 mmol) in ethanol (250 mL) was heated at 60° C. for 1.7 days. Additional triethylamine (17.5 mL) was added and the solution was heated at 60° C. for two more days. The volatiles were removed under reduced pressure and the resulting white solid was triturated with water, isolated by filtration, and dried to provide 4-chloro-2-(ethoxymethyl)-1-prop-2-ynyl-1H-imidazo[4,5-c]quinoline (24.2 g, 96%).

Workup

customThe volatiles were removed under reduced pressure
customthe resulting white solid was triturated with water
customisolated by filtration
customdried

Sources & evidence

ORD record: ord-cf7304308f2b4fde9cb1255a713bbdd0
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915281B2

Reaction notes

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