Dimethyl Sulfoxide → HCID 86653562, compound

HRID 1624998Notes

Reaction equation

HRID 1624998 reaction equation
[C:1]([O:4][CH2:5][CH:6]([N:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2N)[C:13]1=[O:23])[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2].N([O-])=O.[Na+].CS(C)=O.[IH:32].C([O-])(O)=O.[Na+]>>[C:1]([O:4][CH2:5][CH:6]([N:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2[I:32])[C:13]1=[O:23])[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2]

Participants

6

Reactant 5

HCID 679Dimethyl Sulfoxide2×HCID 24841Hydrogen iodideHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 59411435HCID 59411435, compound

Product 1

HCID 86653562HCID 86653562, compound

Conditions

Temperature
35 °C

Procedure

2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)propane-1,3-diyl diacetate (4.2 g, 0.013 mol) was added to a solution of sodium nitrite (4 g, 0.05 mol) in dimethyl sulfoxide (70 mL, 1 mol) at 35° C. Aqueous hydrogen iodide (7 mL, 0.05 mol) in dimethyl sulfoxide (70 mL, 1 mol) was added, the mixture was stirred at 35° C. for 45 minutes. The cooled mixture was neutralized with sat. aq. NaHCO3, extracted with CH2Cl2 (50 mL×3), washed with brine, and dried over MgSO4. Filtered, evaporated and purified via flash column chromatography (12 g of silica gel, 50-100% EtOAc/Hexane) to give the desired product as a yellow oil. MS m/z (M+H) 430.1.

Workup

  1. extractionextracted with CH2Cl2 (50 mL×3)
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationFiltered
  5. customevaporated
  6. custompurified via flash column chromatography (12 g of silica gel, 50-100% EtOAc/Hexane)

Sources & evidence

ORD record
ord-d583c6ec543c482aad6fdfc9a984c615
Source dataset
uspto-grants-2014_07
Patent number
US08779144B2

Reaction notes

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