Acetic Anhydride → 6,7-Dimethoxy-1-methylisoquinolin-3-yl acetate

HRID 1620240Notes

Reaction equation

HRID 1620240 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]([CH3:15])=[N:8][C:7]([OH:16])=[CH:6]2.CCN(C(C)C)C(C)C.[C:26](OC(=O)C)(=[O:28])[CH3:27]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:26]([O:16][C:7]1[N:8]=[C:9]([CH3:15])[C:10]2[C:5]([CH:6]=1)=[CH:4][C:3]([O:2][CH3:1])=[C:12]([O:13][CH3:14])[CH:11]=2)(=[O:28])[CH3:27]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 178486704HCID 178486704, compound2×

Product 1

HCID 681821876,7-Dimethoxy-1-methylisoquinolin-3-yl acetateYield 88%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6,7-dimethoxy-1-methylisoquinolin-3-ol CCH 18060 (3.11 g, 14.19 mmol) in dry CH2Cl2 (230 mL) in a 500 mL round-bottomed flask equipped with a magnetic stirrer was added DIEA (2.46 mL, 14.88 mmol), DMAP (173 mg, 1.42 mmol) and acetic anhydride (1.39 mL, 14.80 mmol) and the reaction mixture was stirred overnight at RT. The organic solution was then washed with brine (50 mL), dried over Na2SO4, filtered and concentrated under vacuum. The residue was finally purified by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 50:50) to give 6,7-dimethoxy-1-methylisoquinolin-3-yl acetate SIL 32158 as an off-white solid (3.26 g, 88% yield).

Workup

  1. washThe organic solution was then washed with brine (50 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe residue was finally purified by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 50:50)

Sources & evidence

ORD record
ord-b1b00fb04df7476a87295e2c00d0ebfe
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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