Dimethyl Sulfoxide → HCID 58270431, compound

HRID 1625008Notes

Reaction equation

HRID 1625008 reaction equation
N[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([CH:13]1[CH2:15][CH2:14]1)[C:7]2=[O:12].N([O-])=O.[Na+].CS(C)=O.[IH:24].C([O-])([O-])=O.[Na+].[Na+]>>[CH:13]1([N:6]2[CH:5]=[CH:4][C:3]3[C:8](=[CH:9][CH:10]=[CH:11][C:2]=3[I:24])[C:7]2=[O:12])[CH2:15][CH2:14]1

Participants

6

Reactant 5

HCID 679Dimethyl Sulfoxide2×HCID 10340Sodium CarbonateHCID 24841Hydrogen iodideHCID 23668193Sodium NitriteHCID 57990560HCID 57990560, compound

Product 1

HCID 58270431HCID 58270431, compound

Procedure

5-Amino-2-cyclopropylisoquinolin-1(2H)-one (2.0 g, 0.0095 mol) was added to a solution of sodium nitrite (3 g, 0.04 mol) in dimethyl sulfoxide (100 mL, 2 mol) at room temperature. Aqueous hydrogen iodide (10 mL, 0.08 mol) in dimethyl sulfoxide (100 mL, 2 mol) was added. The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was neutralized with saturated aq. Na2CO3 and extracted with methylene chloride (3×200 mL). The combined methylene chloride extracts were washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo and the residue was chromatographed on 120 g of silica gel column (0-25% EtOAc/Hexane) to give the desired product as a yellow solid. MS m/z (M+H) 312.2.

Workup

  1. extractionextracted with methylene chloride (3×200 mL)
  2. washThe combined methylene chloride extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed in vacuo
  5. customthe residue was chromatographed on 120 g of silica gel column (0-25% EtOAc/Hexane)

Sources & evidence

ORD record
ord-55ca59dc9f2549bc8f3ac5bd1882fd3a
Source dataset
uspto-grants-2014_07
Patent number
US08779144B2

Reaction notes

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