Pyridine → HCID 3602611, compound

HRID 1194108Notes

Reaction equation

HRID 1194108 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH:18]=[N:17][CH:16]=[CH:15]2.N1C=CC=CC=1>C(Cl)Cl>[C:1]1([S:7]([NH:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[N:17][CH:16]=[CH:15]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 5889916-Aminoisoquinoline

Product 1

HCID 3602611HCID 3602611, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Benzenesulphonyl chloride (4.9 g, 0.028M) in CH2Cl2 (15 ml) was added dropwise over 10 minutes to a cooled stirred mixture of 6-aminoisoquinoline (4.0 g, 0.028M) and pyridine (2.37 g, 0.03M) in CH2Cl2 (150 ml). The reaction mixture was stirred overnight at room temperature and was then washed with H2O. The CH2Cl2 solution was dried over MgSO4 and was then chromatographed on a silica gel column. After evaporation the residue was recrystallised from isopropanol to yield 6-phenylsulphonamidoisoquinoline (2.28 g, 33%), m.p. 204°-6° C.

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. washwas then washed with H2O
  3. dry with materialThe CH2Cl2 solution was dried over MgSO4
  4. customwas then chromatographed on a silica gel column
  5. customAfter evaporation the residue
  6. customwas recrystallised from isopropanol

Sources & evidence

ORD record
ord-3fabdbf927b249b6a987cc2b50035541
Source dataset
uspto-grants-1989_03
Patent number
US04812573

Reaction notes

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