Hydrochloric Acid → 4-Chloro-2-(quinoxaline-5-sulfonylamino)benzoic acid

HRID 2265183Notes

Reaction equation

HRID 2265183 reaction equation
O[Li].O.C[O:5][C:6](=[O:28])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[NH:14][S:15]([C:18]1[C:19]2[N:20]=[CH:21][CH:22]=[N:23][C:24]=2[CH:25]=[CH:26][CH:27]=1)(=[O:17])=[O:16].C1COCC1.Cl>O>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]([OH:28])=[O:5])=[C:8]([NH:14][S:15]([C:18]2[C:19]3[N:20]=[CH:21][CH:22]=[N:23][C:24]=3[CH:25]=[CH:26][CH:27]=2)(=[O:16])=[O:17])[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 671992924-Chloro-2-(quinoxaline-5-sulfonylamino)benzoic acid methyl ester

Product 1

HCID 160907784-Chloro-2-(quinoxaline-5-sulfonylamino)benzoic acidYield 93.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of LiOH.H2O (0.32 g, 7.7 mmol) in water (5 mL) was added to a solution of 4-chloro-2-(quinoxaline-5-sulfonylamino)benzoic acid methyl ester (0.58 g, 1.5 mmol) and THF (10 mL). The biphasic mixture was stirred rapidly at rt for 16 h, then adjusted to pH 5 with 1 M HCl. The resulting precipitate was collected by filtration to afford the acid as a white solid (0.51 g, 92%). MS (ESI+): calcd. for C15H10ClN3O4S, 363.0; m/z found, 364 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 14.20 (br s, 1H), 11.73 (s, 1H), 9.12 (d, J=1.6, 1H), 9.00 (d, J=1.5, 1H), 8.65 (d, J=7.3, 1H), 8.42 (d, J=8.3, 1H), 8.06 (t, J=7.8, 1H), 7.80 (d, J=8.5, 1H), 7.63 (d, J=2.0, 1H), 7.07 (dd, J=8.4, 1.9, 1H).

Workup

  1. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-e82bce7e01d54330a3b4049a402ce2c1
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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