Anthranilic Acid → 5-Sulfoanthranilic acid

HRID 1736378Notes

Reaction equation

HRID 1736378 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(OCC)C.[OH:16][S:17](O)(=[O:19])=[O:18].O=S(=O)=O>>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([S:17]([OH:19])(=[O:18])=[O:16])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 3

HCID 227Anthranilic AcidHCID 3283Diethyl EtherHCID 24681Fuming sulfuric acid

Product 1

HCID 191515-Sulfoanthranilic acidYield 57%

Procedure

A solution of 2-aminobenzoic acid (2g, 15 mM) in oleum (30 ml) was heated at 80°, under argon atmosphere for 2 hours. The mixture was poured into diethyl ether (400 ml) and the resulting precipitate was filtered, washed with diethyl ether and dried under vacuum to give 2-amino-5-sulphobenzoic acid (1.8 g, 57%).

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with diethyl ether
  3. customdried under vacuum

Sources & evidence

ORD record
ord-03f89e8a59c147389fe61d9ee3ba55dc
Source dataset
uspto-grants-1996_07
Patent number
US05541178

Reaction notes

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