Dimethyl Sulfoxide → HCID 67203841, compound

HRID 1624989Notes

Reaction equation

HRID 1624989 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][CH:14]1[CH2:18][O:17][C:16]([CH3:20])([CH3:19])[O:15]1)[C:7]2=[O:12].N([O-])=O.[Na+].CS(C)=O.[IH:29].C([O-])(O)=O.[Na+]>>[CH3:19][C:16]1([CH3:20])[O:15][CH:14]([CH2:13][N:6]2[CH:5]=[CH:4][C:3]3[C:8](=[CH:9][CH:10]=[CH:11][C:2]=3[I:29])[C:7]2=[O:12])[CH2:18][O:17]1

Participants

6

Reactant 5

HCID 679Dimethyl Sulfoxide2×HCID 24841Hydrogen iodideHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 58270448HCID 58270448, compound

Product 1

HCID 67203841HCID 67203841, compound

Procedure

5-Amino-2-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)isoquinolin-1(2H)-one (4.2 g, 0.015 mol) was added to a solution of sodium nitrite (4 g, 0.06 mol) in dimethyl sulfoxide (80 mL, 1 mol) at 35° C. Aqueous hydrogen iodide (8 mL, 0.06 mol) in dimethyl sulfoxide (80 mL, 1 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 magnesium sulfate. The solvent was removed in vacuo and the residue was purified via flash column chromatography (40 g of silica gel, 0-50% EtOAc/Hexane) to give a light yellow solid. MS m/z (M+H) 385.6

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 magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified via flash column chromatography (40 g of silica gel, 0-50% EtOAc/Hexane)
  7. customto give a light yellow solid

Sources & evidence

ORD record
ord-80f4669818fa4e85985b860c2084f982
Source dataset
uspto-grants-2014_07
Patent number
US08779144B2

Reaction notes

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