N-bromobutanimide → HCID 178469667, compound

HRID 1168491Notes

Reaction equation

HRID 1168491 reaction equation
[Br:1]N1C(=O)CCC1=O.[OH:9][C:10]1[C:19]2[C:14](=[C:15]([N+:21]([O-:23])=[O:22])[CH:16]=[C:17]([CH3:20])[CH:18]=2)[N:13]=[CH:12][C:11]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25]>ClCCCl>[Br:1][CH2:20][C:17]1[CH:18]=[C:19]2[C:14](=[C:15]([N+:21]([O-:23])=[O:22])[CH:16]=1)[N:13]=[CH:12][C:11]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:10]2[OH:9]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178469668Ethyl 4-hydroxy-6-methyl-8-nitro-3-quinolinecarboxylate

Product 1

HCID 178469667HCID 178469667, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

N-Bromosuccinimide (3.52 g) is added to a solution of ethyl 4-hydroxy-6-methyl-8-nitro-3-quinolinecarboxylate (2.76 g) in 1,2 dichloroethane (250 mL). The refluxing solution is irradiated with a sun lamp (625 watt) for 20 min. The crude ethyl 6-bromomethyl-4-hydroxy-8-nitro-3-quinolinecarboxylate thus formed is reacted with morpholine (5 mL). After evaporation, the product is partitioned between ethyl acetate and water. Evaporation of the ethyl acetate gives a solid, which is dissolved in chloroform and is chromatographed on silica gel with 1% methanol/chloroform as the initial eluant. Elution of the column with 10% methanol/chloroform gives the title compound, which is crystallized from methanol. Physical characteristics: M.p. 214-216° C. 1H NMR (CDCl3) δ1.41, 2.50, 3.68, 3.74, 4.42, 8.69, 8.73, 8.78, 11.6. Anal. Found: C, 56.30; H, 5.32; N, 11.56.

Workup

  1. customThe refluxing solution is irradiated with a sun lamp (625 watt) for 20 min

Sources & evidence

ORD record
ord-075f39a935f8425a975fa0e22c850ec0
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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