3-Hydroxyanthranilic Acid → 2-Amino-5-chloro-3-hydroxybenzoic acid

HRID 969814Notes

Reaction equation

HRID 969814 reaction equation
[NH2:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(O)(=O)C.S(Cl)([Cl:19])(=O)=O>C(OCC)C>[NH2:1][C:2]1[C:10]([OH:11])=[CH:9][C:8]([Cl:19])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 863-Hydroxyanthranilic AcidHCID 176Acetic AcidHCID 24648Sulfuryl chloride

Product 1

HCID 180011182-Amino-5-chloro-3-hydroxybenzoic acidYield 48%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 25-mL round bottomed flask equipped with a magnetic stirrer was charged with 2-amino-3-hydroxybenzoic acid (0.852 g, 5.59 mmol), acetic acid (0.4 mL) and diethyl ether (0.4 mL). After cooling to 0° C. sulfuryl chloride (0.754 g, 5.59 mmol) was added and the reaction stirred at ambient temperature for 4 h. Dilution with ether (15 mL), filtration and purification by preparative HPLC afforded 0.500 g (48% yield) of 2-amino-5-chloro-3-hydroxybenzoic acid as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.29 (d, J=9.5 Hz, 1H), 6.76 (d, 1H, J=9.5 Hz, 1H) MS (ESI) m/z 186 (M−H).

Workup

  1. customA 25-mL round bottomed flask equipped with a magnetic stirrer
  2. additionwas added
  3. filtrationDilution with ether (15 mL), filtration and purification by preparative HPLC

Sources & evidence

ORD record
ord-4978b1b5e22a4876aeca2876773fc1b5
Source dataset
uspto-grants-2007_12
Patent number
US07307094B2

Reaction notes

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