4-chloro-N-[2-(diethylamino)ethyl]-6-iodoquinoline-3-carboxamide → 4-chloro-N-[2-(diethylamino)ethyl]-6-iodoquinoline-8-carboxamide

HRID 2273665Notes

Reaction equation

HRID 2273665 reaction equation
[CH2:1]([N:3]([CH2:21][CH3:22])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[CH:10]=[C:11]([I:20])[CH:12]=[C:13]2[C:18]=1[NH:17][CH:16]=[CH:15][C:14]2=O)=[O:8])[CH3:2].[Cl:23]C1C2C(=CC=C(I)C=2)N=CC=1C(NCCN(CC)CC)=O>>[Cl:23][C:14]1[C:13]2[C:18](=[C:9]([C:7]([NH:6][CH2:5][CH2:4][N:3]([CH2:21][CH3:22])[CH2:1][CH3:2])=[O:8])[CH:10]=[C:11]([I:20])[CH:12]=2)[N:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 669425004-chloro-N-[2-(diethylamino)ethyl]-6-iodoquinoline-3-carboxamideHCID 66945735N-[2-(diethylamino)ethyl]-6-iodo-4-oxo-1,4-dihydroquinoline-8-carboxamide

Product 1

HCID 669442364-chloro-N-[2-(diethylamino)ethyl]-6-iodoquinoline-8-carboxamideYield 73%

Procedure

This compound was prepared, starting from compound 100 (2.00 g, 4.84 mmol), according to the procedure developed for compound 95. Reaction time at 100° C.: 15 min; the purification was performed using column chromatography (Al2O3, AcOEt/cyclohexane, 9/1, v/v) to give compound 101 (1.52 g, 3.52 mmol) as a beige solid. Yield 73%; Rf (Al2O3, AcOEt/cyclohexane, 9/1, v/v) 0.49; mp 76-78° C.; IR (KBr) ν 1555, 1654, 2962 cm−1; 1H NMR (200 MHz, CDCl3) δ 1.09 (t, 6H, J=7.1 Hz), 2.64 (q, 4H, J=7.1 Hz), 2.75 (t, 2H, J=6.4 Hz), 3.66 (q, 2H, J=6.4 Hz), 7.54 (d. 1H, J=4.7 Hz), 8.68 (d, 1H, J=2.1 Hz), 8.76 (d, 1H, J=4.7 Hz), 9.07 (d, 1H, J=2.1 Hz), 11.01 (m, 1H); MS m/z 433 (M+2, 1), 431 (M+, 1), 360 (1), 358 (1), 317 (1), 315 (3), 289 (1), 287 (1), 191 (1), 189 (2), 161 (3), 126 (2), 99 (9), 86 (100), 71 (2), 58 (9).

Workup

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

Sources & evidence

ORD record
ord-3baf2fe569c045c1ab5f99bfb05b2a64
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

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