Isoquinoline → HCID 67046257, compound

HRID 606316Notes

Reaction equation

HRID 606316 reaction equation
Cl[C:2]([O:4][CH2:5][CH:6]=[CH2:7])=[O:3].[CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][N:9]=1.[CH3:18][C:19]1[C:24]([O:25][CH3:26])=[CH:23][CH:22]=[C:21]([CH3:27])[C:20]=1[Mg]Br>C1COCC1>[CH2:5]([O:4][C:2]([N:9]1[CH:10]=[CH:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]1[C:20]1[C:21]([CH3:27])=[CH:22][CH:23]=[C:24]([O:25][CH3:26])[C:19]=1[CH3:18])=[O:3])[CH:6]=[CH2:7]

Participants

5

Reactant 3

HCID 8405IsoquinolineHCID 18052Allyl chloroformateHCID 178490247HCID 178490247, compound

Product 1

HCID 67046257HCID 67046257, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Allyl chloroformate (2.7 ml, 25 mmol) is added dropwise at 0° C. to a cooled mixture of isoquinoline (2.9 g, 23 mmol) and 2,6-dimethyl-3-methoxyphenylmagnesium bromide (prepared from 7.3 g of 2,6-dimethyl-3-methoxyphenyl bromide and 2.8 g of magnesium turnings) in THF (30 ml). After stirring for 2 h at room temperature, the reaction mixture is quenched with saturated NH4Cl and extracted with Et2O. The combined extracts are washed with saturated brine, dried over Na2SO4, and concentrated to give 6.9 g of 1-(3-methoxy-2,6-dimethyl-phenyl)-1H-isoquinoline-2-carboxylic acid allyl ester.

Workup

  1. customthe reaction mixture is quenched with saturated NH4Cl
  2. extractionextracted with Et2O
  3. washThe combined extracts are washed with saturated brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7cdf1986636544ec85aba0c4018b5e01
Source dataset
uspto-grants-2011_03
Patent number
US07915288B2

Reaction notes

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