p-Toluenesulfonic acid monohydrate → HCID 73057753, compound

HRID 2207330Notes

Reaction equation

HRID 2207330 reaction equation
[OH:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:12][C:13](=[O:21])[C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].O.[C:23]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:23][O:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:12][C:13](=[O:21])[C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:7][CH:6]=1)([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 73057453HCID 73057453, compound

Product 1

HCID 73057753HCID 73057753, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 3-[4-(1-hydroxy-1-methyl-ethyl)-phenyl]-2H-isoquinolin-1-one (83.8 mg, 0.30 mmol) in methanol (1 ml) is added toluene-4-sulfonic acid monohydrate (5.2 mg, 0.030 mmol). The reaction mixture is stirred for 5 days at ambient temperature. The reaction mixture, a white suspension, is evaporated and the residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to afford 3-[4-(1-methoxy-1-methyl-ethyl)-phenyl]-2H-isoquinolin-1-one as white crystals; HPLC/MS 2.66 min (B), [M+H] 294;

Workup

  1. customThe reaction mixture, a white suspension, is evaporated
  2. customthe residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-da260325cd3c4ce981a4afe2a7e4ff70
Source dataset
uspto-grants-2016_06
Patent number
US09376433B2

Reaction notes

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