Dimethylformamide → Methyl 2-cyclopentyl-1-oxo-1,2-dihydroisoquinoline-4-carboxylate

HRID 253128Notes

Reaction equation

HRID 253128 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[NH:7][CH:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[CH:27]1(I)[CH2:31][CH2:30][CH2:29][CH2:28]1>O>[CH:27]1([N:7]2[CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=[O:15])[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 73784IodocyclopentaneHCID 641184Methyl 1-Oxo-2H-Isoquinoline-4-Carboxylate

Product 1

HCID 66844917Methyl 2-cyclopentyl-1-oxo-1,2-dihydroisoquinoline-4-carboxylateYield 23.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methyl-1-oxo-1,2-dihydroisoquinoline-4-carboxylate (780 mg, 3.8 mmol, Bionet), potassium carbonate (650 mg, 4.7 mmol, Aldrich), and 6 mL of DMF was added cyclopentyl iodide (0.52 mL, 4.5 mmol, Aldrich). The solution was stirred at RT for 4 h, then diluted with 50 mL of water. The solids were filtered and washed with CH2Cl2 and EtOAc. The filtrate was concentrated in vacuo and chromatographed through a Redi-Sep® pre-packed silica gel column (12 g), eluting with 0% to 15% EtOAc:hexane to give 240 mg (23%) of methyl 2-cyclopentyl-1-oxo-1,2-dihydroisoquinoline-4-carboxylate as an off-white solid. MS m/z: 272.3(M+1).

Workup

  1. filtrationThe solids were filtered
  2. washwashed with CH2Cl2 and EtOAc
  3. concentrationThe filtrate was concentrated in vacuo
  4. customchromatographed through a Redi-Sep® pre-packed silica gel column (12 g)
  5. washeluting with 0% to 15% EtOAc

Sources & evidence

ORD record
ord-98c1e23645c7400dbf81e0f5d7c94dab
Source dataset
uspto-grants-2011_01
Patent number
US07872009B2

Reaction notes

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