Citric Acid → 5-Methanesulfonamidoisoquinoline

HRID 480029Notes

Reaction equation

HRID 480029 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][N:11]=[CH:12]2.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>N1C=CC=CC=1>[CH3:1][S:2]([NH:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][N:11]=[CH:12]2)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 31297Methanesulfonyl chlorideHCID 707665-Aminoisoquinoline

Product 1

HCID 187652015-MethanesulfonamidoisoquinolineYield 46%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulfonyl chloride (3.2 ml, 42 mmol) was added to a solution of 5-aminoisoquinoline (5.0 g, 35 mmol) in pyridine (40 ml) and the mixture was allowed to stand for 72 h. The reaction mixture was then poured into aqueous citric acid (10%, 400 ml) and extracted with EtOAc (2×230 ml). The organic layer was evaporated to give a residue that was purified on silica gel, eluting with CH2Cl2/MeOH, to afford the subtitle compound as a solid (3.55 g, 46%). Rf 0.03 (CH2Cl2/ether 4/1, v/v). 1H NMR (D6-DMSO) δ: 3.07 (3H, s), 7.68 (1H, t), 7.75 (1H, d), 8.03 (1H, d), 8.10 (1H, d), 8.54 (1H, d), 9.32 (1H, s), 9.79 (1H, bs).

Workup

  1. extractionextracted with EtOAc (2×230 ml)
  2. customThe organic layer was evaporated
  3. customto give a residue that
  4. customwas purified on silica gel
  5. washeluting with CH2Cl2/MeOH

Sources & evidence

ORD record
ord-a76aaea4d49f4fb7b4719bee096be387
Source dataset
uspto-grants-2003_11
Patent number
US06649620B2

Reaction notes

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