N-bromobutanimide → N-(6-(bromomethyl)quinolin-2-yl)acetamide

HRID 1503154노트

반응식

HRID 1503154 반응식
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:15])[CH:11]=2)[N:6]=1)(=[O:3])[CH3:2].[Br:16]N1C(=O)CCC1=O>C1C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:15][Br:16])[CH:11]=2)[N:6]=1)(=[O:3])[CH3:2]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 11458305N-(6-methylquinolin-2-yl)acetamide

생성물 1

HCID 11300436N-(6-(bromomethyl)quinolin-2-yl)acetamide수율 63%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 241Benzene용매

실험 절차

Compound 45 (0.300 g, 1.50 mmol) was diluted in anhydrous benzene (10 mL). N-Bromosuccinimide (0.280 g, 1.57 mmol) and a catalytic amount (˜0.020 g) of benzoyl peroxide were added, and the mixture was heated to reflux under nitrogen until an orange tint was no longer visible in the solution refluxing in the condenser (around 2 h 40 min). The mixture was cooled, concentrated, and purified by flash column chromatography (SiO2), eluting with a gradient of 10% to 12% EtOAc in CH2Cl2 to yield the product (0.262 g, 63%) as a flocculent yellow solid. The 1H NMR chemical shifts for this compound are identical to those previously reported in the literature. 1H-NMR (500 MHz; CDCl3): δ 8.44 (br d, J=8.6 Hz, 1 H), 8.30 (br s, 1 H), 8.17 (d, J=9.0 Hz, 1 H), 7.82 (m, J=9.1 Hz, 2 H), 7.72 (dd, J=8.6, 2.1 Hz, 1 H), 4.67 (s, 2 H), 2.29 (s, 3 H).

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux under nitrogen until an orange tint
  3. temperaturerefluxing in the condenser (around 2 h 40 min)
  4. temperatureThe mixture was cooled
  5. concentrationconcentrated
  6. custompurified by flash column chromatography (SiO2)
  7. washeluting with a gradient of 10% to 12% EtOAc in CH2Cl2

출처 및 근거

ORD 기록
ord-dff293a5e612415591e5165a5d333534
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212144B2

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