4-chloro-N-[2-(diethylamino)ethyl]-6-iodoquinoline-3-carboxamide → 4-chloro-N-[2-(diethylamino)ethyl]-6-iodoquinoline-2-carboxamide

HRID 2273668Notes

Reaction equation

HRID 2273668 reaction equation
[CH2:1]([N:3]([CH2:21][CH3:22])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[NH:10][C:11]2[C:16]([C:17](=O)[CH:18]=1)=[CH:15][C:14]([I:20])=[CH:13][CH:12]=2)=[O:8])[CH3:2].[Cl:23]C1C2C(=CC=C(I)C=2)N=CC=1C(NCCN(CC)CC)=O>>[Cl:23][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([I:20])[CH:15]=2)[N:10]=[C:9]([C:7]([NH:6][CH2:5][CH2:4][N:3]([CH2:21][CH3:22])[CH2:1][CH3:2])=[O:8])[CH:18]=1

Participants

3

Reactant 2

HCID 669425004-chloro-N-[2-(diethylamino)ethyl]-6-iodoquinoline-3-carboxamideHCID 70794488N-[2-(diethylamino)ethyl]-6-iodo-4-oxo-1,4-dihydroquinoline-2-carboxamide

Product 1

HCID 581519944-chloro-N-[2-(diethylamino)ethyl]-6-iodoquinoline-2-carboxamideYield 91%

Procedure

This compound was prepared, starting from compound 104 (0.34 g, 0.82 mmol), according to the procedure developed for compound 95. Reaction time at 100° C.: 15 min; the purification was performed using column chromatography (Al2O3, CH2Cl2/EtOH, 99/1, v/v) to give compound 105 (323 mg, 0.75 mmol) as a beige solid. Yield 91%; Rf (Al2O3, CH2Cl2/EtOH, 99/1, v/v) 0.42; mp 64-66° C.: IR (KBr) ν 1182, 1297, 1386, 1479, 1518, 1691, 2811, 2965, 3354 cm−1; 1H NMR (200 MHz, CDCl3) δ 1.11 (t, 6H, J=7.1 Hz), 2.66 (q, 4H, J=7.1 Hz), 2.75 (t, 2H, J=6.2 Hz), 3.60 (q, 2H, J=6.1 Hz), 7.82 (d, 1H, J=8.9 Hz), 8.03 (dd, 1H, J=1.8, 8.9 Hz), 8.36 (s, 1H), 8.56 (m, 1H), 8.64 (d, 1H, J=1.8 Hz); ESI-MS m/z 431.8 [M+H]+.

Workup

  1. customThis compound was prepared
  2. customReaction time at 100° C.
  3. custom15 min
  4. customthe purification

Sources & evidence

ORD record
ord-1b4c52b953394f2e8d479f828a2139dd
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

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