Chlorosuccinimide → HCID 86656171, compound

HRID 1192487Notes

Reaction equation

[OH:1][C:2]1[C:3]([C:12]([N:14]([O:16][CH3:17])[CH3:15])=[O:13])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[Cl:18]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:18][C:5]1[CH:4]=[C:3]([C:12]([N:14]([O:16][CH3:17])[CH3:15])=[O:13])[C:2]([OH:1])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 8-hydroxy-N-methoxy-N-methylquinoline-7-carboxamide (5.00 g, 21.5 mmol) in acetic acid (100 mL) was added N-chlorosuccinimide (3.16 g, 23.7 mmol) and the resulting mixture heated at 100° C. for 18 hours. After allowing the mixture to cool to ambient temperature, the reaction mixture was concentrated in vacuo, then neutralized with saturated sodium bicarbonate, and then extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and then concentrated to dryness under reduced pressure. The residue was purified on silica gel, eluting with 0 to 10% methanol in dichloromethane, to give the desired product (4.68 g, 81%). LCMS calculated for C12H12ClN2O3(M+H)+: m/z=267.1; found: 267.0. 1H NMR (DMSO-d6, 400 MHz) δ 90.4 (1H, dd, J=4.0 and 1.2 Hz), 8.61 (1H, dd, J=8.8 and 1.6 Hz), 7.92 (1H, s), 7.80 (1H, dd, J=8.8 and 4.4 Hz), 3.45 (3H, s), 3.30 (4H, br s) ppm.

Workup

temperatureto cool to ambient temperature
concentrationthe reaction mixture was concentrated in vacuo
extractionextracted with ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated to dryness under reduced pressure
customThe residue was purified on silica gel
washeluting with 0 to 10% methanol in dichloromethane

Sources & evidence

ORD record: ord-bc602a7c22dd43d58ae8caa541029f68
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680108B2

Reaction notes

Loading…