Hydrochloric Acid → Methyl (3-carboxy-propionylamino)-2-hydroxybenzoate

HRID 1969156Notes

Reaction equation

HRID 1969156 reaction equation
S(=O)(=O)(O)O.N[C:7]1[CH:8]=[C:9]([OH:17])[C:10](=[CH:15][CH:16]=1)[C:11]([O:13][CH3:14])=[O:12].C(Cl)Cl.[C:21]1(=[O:27])[O:26][C:24](=[O:25])[CH2:23][CH2:22]1.Cl.C([N:31](CC)CC)C>>[C:21]([CH2:22][CH2:23][C:24]([NH:31][C:8]1[C:9]([OH:17])=[C:10]([CH:15]=[CH:16][CH:7]=1)[C:11]([O:13][CH3:14])=[O:12])=[O:25])([OH:26])=[O:27]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 68720411Methyl 4-aminosalicylate bisulfate

Product 1

HCID 86616494Methyl (3-carboxy-propionylamino)-2-hydroxybenzoate

Procedure

Methyl 4-aminosalicylate bisulfate (5 g) is placed in a 50-mL round bottom flask. The flask is charged with 20 mL of methylene chloride and 15 mL of triethylamine. Finally, succinic anhydride (2.75 g) is added. The reaction mixture is then allowed to stir at ambient conditions overnight. Solvents are removed under reduced pressure, yielding a viscous residue, to which 1 N HCl is added. Methyl (3-carboxy-propionylamino)-2-hydroxybenzoate is yielded as tan powder. The powders are collected by filtration, washed with water, and dried.

Workup

  1. customSolvents are removed under reduced pressure
  2. customyielding a viscous residue

Sources & evidence

ORD record
ord-d23666e45bd04082931f55550a422c1e
Source dataset
uspto-grants-2013_04
Patent number
US08426466B2

Reaction notes

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