Sodium Iodide → 7-chloro-3-(3,5-dimethylphenyl)-4-[2-(1-methylpiperidin-2-yl)-ethoxy]-6-nitro-1H-quinolin-2-one

HRID 1857622Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:21])=[C:7]([C:13]3[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[N+:22]([O-:24])=[O:23].C(=O)(O)[O-].[Na+].[I-].[Na+].Cl.Cl[CH2:34][CH2:35][CH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][N:37]1[CH3:42]>CN(C)C=O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:21][CH2:34][CH2:35][CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][N:37]3[CH3:42])=[C:7]([C:13]3[CH:14]=[C:15]([CH3:20])[CH:16]=[C:17]([CH3:19])[CH:18]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[N+:22]([O-:24])=[O:23]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 7-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-6-nitro-1H-quinolin-2-one (100 mg) and sodium bicarbonate (54 mg) was suspended in 2 mL dry N,N-dimethylformamide and heated to 80° C. on an oil bath. After 30 minutes, sodium iodide (48 mg) was added followed by 2-(2-chloroethyl)-1-methylpiperidine hydrochloride (64 mg) and the mixture stirred at 80° C. for 7 hours. At this time the reaction was cooled to room temperature and quenched by the addition of 25 mL ice/water. The mixture was filtered and the residue washed (1×) with ice water then dried at 40° C. Purification of the crude product by flash chromatography on silica gel (chloroform:10% ammonium hydroxide in methanol, 95:5) gave the title compound (67 mg).

Workup

temperatureAt this time the reaction was cooled to room temperature
customquenched by the addition of 25 mL ice/water
filtrationThe mixture was filtered
washthe residue washed (1×) with ice water
customthen dried at 40° C
customPurification of the crude product by flash chromatography on silica gel (chloroform:10% ammonium hydroxide in methanol, 95:5)

Sources & evidence

ORD record: ord-cf5fe14dfd464d14a753b1d117efa825
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06147088

Reaction notes

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