Hydrochloric Acid → 2-Hydroxy-5-(pyrrolidine-1-sulfonyl)benzoic acid

HRID 2263946Notes

Reaction equation

HRID 2263946 reaction equation
Cl[S:2]([C:5]1[CH:6]=[CH:7][C:8]([OH:14])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])(=[O:4])=[O:3].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.Cl>O1CCCC1>[OH:14][C:8]1[CH:7]=[CH:6][C:5]([S:2]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)(=[O:4])=[O:3])=[CH:13][C:9]=1[C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 27772405-(Chlorosulfonyl)-2-hydroxybenzoic acid

Product 1

HCID 16528482-Hydroxy-5-(pyrrolidine-1-sulfonyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-chlorosulfonyl-2-hydroxybenzoic acid (0.52 g, 2.0 mmol, Matrix Scientific) in tetrahydrofuran (10 mL) was treated with pyrrolidine (1.5 g, 21 mmol) and refluxed for 2 h. This was cooled and poured into dilute aqueous hydrochloric acid and extracted into dichloromethane (2×50 mL). The combined extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated to give a solid. This was triturated with ether to give 2-hydroxy-5-(pyrrolidine-1-sulfonyl)benzoic acid as a solid. It was then converted to 2-ethoxy-5-(pyrrolidine-1-sulfonyl)benzoic acid ethyl ester In a manner analogous to the method described in example 33.

Workup

  1. temperaturerefluxed for 2 h
  2. temperatureThis was cooled
  3. extractionextracted into dichloromethane (2×50 mL)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a solid
  9. customThis was triturated with ether

Sources & evidence

ORD record
ord-372f7272303f40988c9236daf7dbcff6
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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