Sulfuric Acid → 6-Methoxy-7-methylquinoline

HRID 931742

反応式

HRID 931742 の反応式
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][C:4]=1[CH3:10].OS(O)(=O)=O.[N+]([C:19]1[CH:20]=C(S(O)(=O)=O)C=C[CH:24]=1)([O-])=O>OCC(CO)O>[CH3:1][O:2][C:3]1[CH:9]=[C:8]2[C:6](=[CH:5][C:4]=1[CH3:10])[N:7]=[CH:20][CH:19]=[CH:24]2

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 73873-Nitrobenzenesulfonic acidHCID 672973-Methyl-4-methoxybenzenamine

生成物 1

HCID 155348986-Methoxy-7-methylquinoline収率 77.2%

試薬・触媒・溶媒 1

HCID 753Glycerol溶媒

反応条件

温度
140 °C

実験手順

To 4-methoxy-3-methylaniline (6.7 g) was added concentrated H2SO4 (12.4 mL), followed by glycerin (21.1 g), m-nitrobenzenesulfonic acid (6.53 g), H3BO3 (3.4 g) and FeSO47H2O (3.2 g). The mixture was stirred at 140° C. for 1 h. The reaction was cooled to 25° C., quenched with ice-water and neutralized with 30% KOH. The mixture was extracted with DCM (2×), and the combined extracts dried with Na2SO4 and concentrated in vacuo. The crude product was purified by column chromatography (EtOAc) to give 6-methoxy-7-methylquinoline (4.3 g) LCMS-ESI+ (m/z): 174.1 (M+H)+.

後処理

  1. temperatureThe reaction was cooled to 25° C.
  2. customquenched with ice-water and neutralized with 30% KOH
  3. extractionThe mixture was extracted with DCM (2×)
  4. dry with materialthe combined extracts dried with Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography (EtOAc)

出典と根拠

ORDレコード
ord-a1397495688b44dcb6a1dc1af372a924
出典データセット
uspto-grants-2016_03
特許番号
US09296758B2

関連ノート

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