Perchloric Acid → HCID 68352842, compound

HRID 572529Notes

Reaction equation

HRID 572529 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[N:11]([CH3:20])[C:10]=1[CH:21]([OH:26])[C:22]([O:24][CH3:25])=[O:23].Cl(O)(=O)(=O)=O>C(OC(C)(C)C)(=O)C>[CH3:1][C:2]([O:26][CH:21]([C:10]1[N:11]([CH3:20])[C:12](=[O:19])[C:13]2[C:18]([C:9]=1[C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1])=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:22]([O:24][CH3:25])=[O:23])([CH3:7])[CH3:3]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 68295591HCID 68295591, compound

Product 1

HCID 68352842HCID 68352842, compound

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

A mixture of methyl 2-(4-(2,4-dimethylphenyl)-2-methyl-1-oxo-1,2-dihydroisoquinolin-3-yl)-2-hydroxyacetate (858 mg, 2.442 mmol) in t-butyl acetate (20 mL) was treated with perchloric acid (0.147 mL, 2.442 mmol) and stirred at ambient temperature overnight. LCMS indicated only 45% conversion to the desired product. The mixture was made basic by adding 3N sodium hydroxide and then extracted with ethyl acetate. The extracts were washed with water, then brine, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel (0-50% ethyl acetate/hexanes gradient) to afford the desired product as a colorless residue (383 mg, 39%). LC/MS (m/z) ES+=408 (M+1).

Sources & evidence

ORD record
ord-441be7f771d449a7b3d0c035c91fdd22
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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