Trisodium Phosphate → HCID 86627545, compound

HRID 1970042Notes

Reaction equation

Cl[S:2]([C:5]1[CH:14]=[CH:13][C:12]2[NH:11][C:10](=[O:15])[C:9]3[NH:16][CH:17]=[C:18]([C:19]([OH:21])=[O:20])[C:8]=3[C:7]=2[CH:6]=1)(=[O:4])=[O:3].S([O-])([O-])=O.[Na+].[Na+].P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].[Cl:36][C:37]1[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[C:38]=1[CH2:39]Br>O.CN(C)C=O>[Cl:36][C:37]1[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[C:38]=1[CH2:39][S:2]([C:5]1[CH:14]=[CH:13][C:12]2[NH:11][C:10](=[O:15])[C:9]3[NH:16][CH:17]=[CH:18][C:8]=3[C:7]=2[CH:6]=1)(=[O:3])=[O:4].[CH2:18]([C:19]([O-:21])=[O:20])[CH3:17]

Participants

Conditions

Temperature: 60 °C

Procedure

180 mg (0.55 mmol) of 8-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid is added to a solution of 139 mg (1.1 mmol) of sodium sulfite and 78 mg (0.55 mmol) of dibasic sodium phosphate dissolved in 2.5 mL of water. The solution is heated at 60° C. for 20 hours then a solution of 132 mg (0.55) of 2,6-dichlorobenzyl bromide in 2.5 mL of dimethylformamide is added. Stirring is continued at 60° C. for 4 hours then the solution is filtered. The solid is triturated in hot methanol then filtered again to give 88 mg (35%) of 8-(2,6-dichlorophenylmethanesulfonyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid.

Workup

filtrationthe solution is filtered
customThe solid is triturated in hot methanol
filtrationthen filtered again

Sources & evidence

ORD record: ord-c5951a33ed334d7183249d0422b51cff
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426437B2

Reaction notes

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