Sulfuric Acid → HCID 22176077, compound

HRID 1797610Notes

Reaction equation

HRID 1797610 reaction equation
[NH2:1][CH2:2][C:3]1[N:4]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:5](=[O:21])[C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:10][C:9]([S:19][CH3:20])=[CH:8][CH:7]=2.S(=O)(=O)(O)[OH:27].OOS([O-])=O.[K+].C(=O)([O-])O.[Na+]>O.CO>[NH2:1][CH2:2][C:3]1[N:4]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:5](=[O:21])[C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:10][C:9]([S:19]([CH3:20])=[O:27])=[CH:8][CH:7]=2

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 22175707HCID 22175707, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 22176077HCID 22176077, compoundYield 70.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 3-(aminomethyl)-2-isobutyl-6-(methylsulfanyl)-4-phenyl-1(2H)-isoquinolinone (0.18 g, 0.52 mmol), conc. sulfuric acid (0.0168 mL, 0.31 mmol), methanol (2 mL) and water (5 mL) was added Oxone® (0.19 g, 0.31 mmol), and the mixture was stirred at room temperature for 30 min. The reaction mixture was poured into saturated, aqueous sodium hydrogencarbonate (50 mL) and extracted 3 times with ethyl acetate (25 mL). The extracts were combined, washed with saturated brine (10 mL), dried over anhydrous magnesium sulfate (9 g) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:1 (v/v)). The resulting oil was solidified from diisopropyl ether (1 mL) to give the title compound (0.081 g, 42%) as a pale-yellow powder.

Workup

  1. extractionextracted 3 times with ethyl acetate (25 mL)
  2. washwashed with saturated brine (10 mL)
  3. dry with materialdried over anhydrous magnesium sulfate (9 g)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:1 (v/v))

Sources & evidence

ORD record
ord-0e9340993dc34260a0cfcfb710d0d5fc
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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