Acetic Anhydride → 1-(4,4-dimethyl-7-nitro-3,4-dihydro-1H-isoquinolin-2-yl)ethanone

HRID 969671ノート

反応式

HRID 969671 の反応式
[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=2)[CH2:5][NH:4][CH2:3]1.CCN(C(C)C)C(C)C.[CH3:25][C:26](OC(C)=O)=[O:27]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=2)[CH2:5][N:4]([C:26](=[O:27])[CH3:25])[CH2:3]1

参加物

6

反応物 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 219596554,4-Dimethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline

生成物 1

HCID 219595651-(4,4-dimethyl-7-nitro-3,4-dihydro-1H-isoquinolin-2-yl)ethanone

試薬・触媒・溶媒 2

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

実験手順

A mixture of 4-(dimethylamino)pyridine (0.125 g, 1.02 mmol), 4,4-dimethyl-7-nitro-1,2,3,4-tetrahydro-isoquinoline (0.21 g, 1.02 mmol), DIEA (0.53 mL, 3.06 mmol), and Ac2O (0.19 mL, 2.04 mmol) in 7 mL of CH2Cl2 was stirred at RT under N2 for two days. The volatiles were removed under vacuum. The residue was partitioned between EtOAc and brine, and the organic portion was dried with Na2SO4, filtered, and concentrated. The crude material was purified by flash column chromatography (2-3% MeOH in CH2Cl2), to yield the desired compound as a light yellowish solid. MS (ES+): 249.3 (M+H)+. Calc'd for C13H16N2O3-248.28.

後処理

  1. customThe volatiles were removed under vacuum
  2. customThe residue was partitioned between EtOAc and brine
  3. dry with materialthe organic portion was dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by flash column chromatography (2-3% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-d1f9a01c9f3e470587ef7c783abd9c66
出典データセット
uspto-grants-2007_12
特許番号
US07307088B2

反応ノート

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