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

HRID 969671노트

반응식

HRID 969671 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d1f9a01c9f3e470587ef7c783abd9c66
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07307088B2

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