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

HRID 1620240ノート

反応式

HRID 1620240 の反応式
[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]

参加物

6

反応物 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 178486704HCID 178486704、化合物2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b1b00fb04df7476a87295e2c00d0ebfe
出典データセット
uspto-grants-2014_07
特許番号
US08772316B2

反応ノート

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