Dimethyl Sulfoxide → HCID 67203524, compound

HRID 1624993Notes

Reaction equation

HRID 1624993 reaction equation
N[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([CH2:13][CH2:14][OH:15])[C:7]2=[O:12].N([O-])=O.[Na+].CS(C)=O.[IH:24].C([O-])(O)=O.[Na+]>>[OH:15][CH2:14][CH2:13][N:6]1[CH:5]=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[I:24])[C:7]1=[O:12]

Participants

6

Reactant 5

HCID 679Dimethyl Sulfoxide2×HCID 24841Hydrogen iodideHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 59515749HCID 59515749, compound

Product 1

HCID 67203524HCID 67203524, compound

Procedure

5-Amino-2-(2-hydroxyethyl)isoquinolin-1(2H)-one (1.62 g, 0.00793 mol) was added to a solution of sodium nitrite (2 g, 0.03 mol) in dimethyl sulfoxide (40 mL, 0.5 mol) at 35° C. Aqueous hydrogen iodide (4 mL, 0.03 mol) in dimethyl sulfoxide (40 mL, 0.5 mol) was added, and the reaction mixture was stirred for 1 hour. The cooled reaction mixture was neutralized with sat. aq. NaHCO3 and extracted with methylene chloride (3×50 mL). The combined methylene chloride extracts were washed with brine, dried over sodium sulfate and reduced in vacuo. The mixture was purified by column chromatography using an ethyl acetate:hexanes (0-100) gradient. The combined pure fractions were reduced in vacuo to yield the title compound as an off white solid.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with methylene chloride (3×50 mL)
  3. washThe combined methylene chloride extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customThe mixture was purified by column chromatography

Sources & evidence

ORD record
ord-d53c4c55486b440bb924d6bec94900b1
Source dataset
uspto-grants-2014_07
Patent number
US08779144B2

Reaction notes

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