m-Chloroperbenzoic acid → HCID 90387073, compound

HRID 1476802Notes

Reaction equation

HRID 1476802 reaction equation
[C:1]1([C:11]([O:13][CH3:14])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.ClC1C=C(C=CC=1)C(OO)=[O:20]>C(Cl)Cl>[CH3:14][O:13][C:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N+:2]=1[O-:20])=[O:12]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21196988Methyl isoquinoline-1-carboxylate

Product 1

HCID 90387073HCID 90387073, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of methyl isoquinoline-1-carboxylate (11.2 g, 59.8 mmol) in DCM (150 mL) was added 3-chloroperoxybenzoic acid (15.5 g, 89.7 mmol) at 0° C. The mixture was warmed to RT and was stirred at RT for 24 hours. The reaction was quenched with saturated aqueous NaHCO3 and the mixture was extracted with DCM. The organic layer was separated and dried over Na2SO4, and the solvent was evaporated under reduced pressure. The crude product was purified by silica gel chromatography eluting with petroleum ether and EtOAc (1:1) to give the title compound as a white solid (9.5 g, 78%). ESI-MS m/z [M+H]+ 204.

Workup

  1. customThe reaction was quenched with saturated aqueous NaHCO3
  2. extractionthe mixture was extracted with DCM
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. customthe solvent was evaporated under reduced pressure
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with petroleum ether and EtOAc (1:1)

Sources & evidence

ORD record
ord-6bc19baffa704269b3c4f8b25397834c
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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