5-Aminosalicylic Acid → 2-hydroxy-4-[(phenoxycarbonyl)amino]benzoic acid

HRID 1464556Notes

Reaction equation

HRID 1464556 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].[NH2:12][C:13]1[CH:21]=[C:17]([C:18]([OH:20])=[O:19])[C:16]([OH:22])=[CH:15][CH:14]=1.[C:23]1([O:29][C:30](Cl)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])O.[Na+]>>[C:23]1([O:29][C:30]([NH:1][C:2]2[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=2)[C:6]([OH:8])=[O:7])=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:23]1([O:29][C:30]([NH:12][C:13]2[CH:21]=[C:17]([C:18]([OH:20])=[O:19])[C:16]([OH:22])=[CH:15][CH:14]=2)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 40755-Aminosalicylic AcidHCID 46494-Aminosalicylic AcidHCID 15891Phenyl chloroformateHCID 516892Sodium Bicarbonate

Product 2

HCID 2499942-hydroxy-4-[(phenoxycarbonyl)amino]benzoic acidHCID 249995HCID 249995, compound

Procedure

In the preparation process described in J. Pharm. Sci., 52, 927 (1963), 4-aminosalicylic acid and 5-aminosalicylic acid is reacted with phenylchloroformate in an aqueous sodium hydrogen carbonate solution to obtain 4-phenyloxycarbonylaminosalicylic acid and 5-phenyloxycarbonylaminosalicylic acid, respectively, in the relatively high yield.

Sources & evidence

ORD record
ord-f1ea4df59e7e4c3a87eec08fa2fc3995
Source dataset
uspto-grants-1994_04
Patent number
US05306688

Reaction notes

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