Methyl 3-amino-4-hydroxybenzoate → 3-(5-Chloro-2-methoxy-benzenesulfonylamino)-4-hydroxy-benzoic acid methyl ester

HRID 1660824Notes

Reaction equation

HRID 1660824 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH3:13])=[C:6]([S:8](Cl)(=[O:10])=[O:9])[CH:7]=1.[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([NH2:24])[CH:18]=1>N1C=CC=CC=1>[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([NH:24][S:8]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:12][CH3:13])(=[O:10])=[O:9])[CH:18]=1

Participants

4

Reactant 2

HCID 10815Methyl 3-amino-4-hydroxybenzoateHCID 27342725-Chloro-2-methoxybenzene-1-sulfonyl chloride

Product 1

HCID 667891293-(5-Chloro-2-methoxy-benzenesulfonylamino)-4-hydroxy-benzoic acid methyl esterYield 809.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Chloro-2-methoxybenzenesulfonyl chloride (5.77 g, 2.39 mmol) was added to a solution of 3-amino-4-hydroxy-benzoic acid methyl ester (example 1, step 1; 4.00 g, 23.9 mmol) in pyridine (38 mL). The homogeneous solution was stirred at room temperature for 72 h, then partitioned between ethyl acetate and 2 M aq. hydrochloric acid solution. The organic layer was washed with brine, dried (MgSO4), and evaporated. The residue was triturated in ethyl acetate to furnish 3-(5-chloro-2-methoxy-benzenesulfonylamino)-4-hydroxy-benzoic acid methyl ester (7.19 g, 81%). Pink solid, MS (ISP)=370.0 (M−H)−.

Workup

  1. custompartitioned between ethyl acetate and 2 M aq. hydrochloric acid solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was triturated in ethyl acetate

Sources & evidence

ORD record
ord-a2daddc99298490cae93effcf31f1e5f
Source dataset
uspto-grants-2011_10
Patent number
US08030308B2

Reaction notes

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