Nitric Acid → 2-Methyl-7-nitro-1,2,3,4-tetrahydroquinoline

HRID 494189

反応式

HRID 494189 の反応式
[CH3:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[N+:12]([O-])([OH:14])=[O:13].[OH-].[Na+]>S(=O)(=O)(O)O>[CH3:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[CH:7][CH:8]=2)[NH:3]1

参加物

5

反応物 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 962892-Methyl-1,2,3,4-tetrahydroquinoline

生成物 1

HCID 690406212-Methyl-7-nitro-1,2,3,4-tetrahydroquinoline

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

反応条件

温度
2.5 °C

実験手順

To a solution of 2-methyl-1,2,3,4-tetrahydroquinoline (D63) (383 mg, 2.6 mmol) in concentrated sulfuric acid (7.2 ml) at 0-5° C. was added concentrated nitric acid (0.26 ml) dropwise so as to maintain the temperature at 0-5° C. On completion of addition, the mixture was warmed to room temperature, stirred for 45 mins. then poured onto crushed ice and neutralised with 2M sodium hydroxide solution. The mixture was extracted with DCM which was washed with brine, dried over MgSO4 and concentrated in vacuo to give the crude product which was purified by flash column chromatography. Elution with 10% EtOAc in 60-80° C. petroleum ether gave the title compound as an orange solid (297 mg). 1H NMR (400 MHz, CDCl3) δ (ppm): 7.40 (dd, 1H), 7.27 (d, 1H), 7.03 (d, 1H), 4.01 (br, 1H), 3.46 (m, 1H), 2.87 (m, 2H), 1.92 (m, 1H), 1.59 (m, 1H), 1.24 (d, 3H).

後処理

  1. additionOn completion of addition
  2. temperaturethe mixture was warmed to room temperature
  3. additionthen poured
  4. customonto crushed ice
  5. extractionThe mixture was extracted with DCM which
  6. washwas washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customto give the crude product which
  10. customwas purified by flash column chromatography
  11. washElution with 10% EtOAc in 60-80° C. petroleum ether

出典と根拠

ORDレコード
ord-501884145ff140e59d22e26d12c64f9d
出典データセット
uspto-grants-2009_05
特許番号
US07538121B2

関連ノート

読み込み中…