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

HRID 1503154ノート

反応式

HRID 1503154 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒HCID 241Benzene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-dff293a5e612415591e5165a5d333534
出典データセット
uspto-grants-2015_12
特許番号
US09212144B2

反応ノート

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