Methanol → N-(2-Aminoethyl)-1-chloroisoquinoline-5-sulfonamide

HRID 2219204Notes

Reaction equation

HRID 2219204 reaction equation
[OH-].[Na+].Cl.[NH2:4][CH2:5][CH2:6][NH:7][S:8]([C:11]1[C:12]2[CH:13]=[CH:14][N:15]=[C:16]([Cl:21])[C:17]=2[CH:18]=[CH:19][CH:20]=1)(=[O:10])=[O:9].CO>C1COCC1>[NH2:4][CH2:5][CH2:6][NH:7][S:8]([C:11]1[C:12]2[CH:13]=[CH:14][N:15]=[C:16]([Cl:21])[C:17]=2[CH:18]=[CH:19][CH:20]=1)(=[O:9])=[O:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 866109261-Chloro-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide hydrochloride

Product 1

HCID 13730021N-(2-Aminoethyl)-1-chloroisoquinoline-5-sulfonamideYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 5N NaOH solution (0.937 mL) is added slowly to a stirred suspension of 1-chloro-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide hydrochloride (1.51 g, 4.69 mmol) in THF (20 mL)/CH3OH (20 mL) at ambient temperature to form a clear solution. After concentration in vacuo, the tan solid is suspended in EtOAc/CH3OH and sonicated for a few minutes. The mixture is filtered and concentrated to give 1.21 g (4.23 mmol, 90% yield) of the title compound as a tan powder. ESIMS: m/z 286 [(M+H)+, 35Cl], 288 [(M+H)+, 37Cl].

Workup

  1. customto form a clear solution
  2. concentrationAfter concentration in vacuo
  3. customsonicated for a few minutes
  4. filtrationThe mixture is filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2390295f1cec464faaf21eb06cee041a
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

Loading…