Acetic Acid → HCID 59303232、化合物

HRID 2238390ノート

反応式

HRID 2238390 の反応式
[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[C:12]([N+:16]([O-:18])=[O:17])=[CH:13][CH:14]=[CH:15][C:9]=3[CH:8]=[CH:7][C:6]=2[N:5](C(=O)C(F)(F)F)[CH2:4]1.C([O-])([O-])=O.[Cs+].[Cs+].CC(O)=O>O1CCOCC1.O.CO>[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[C:12]([N+:16]([O-:18])=[O:17])=[CH:13][CH:14]=[CH:15][C:9]=3[CH:8]=[CH:7][C:6]=2[NH:5][CH2:4]1

参加物

7

反応物 3

HCID 176Acetic AcidHCID 10796Cesium carbonateHCID 44549147HCID 44549147、化合物

生成物 1

HCID 59303232HCID 59303232、化合物収率 91.4%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of 132 (1.54 g, 4.29 mmol) in dioxane (10 mL) was treated with a solution of Cs2CO3 (3.26 g, 10 mmol) in water (3 mL) and MeOH (7 mL) and the mixture was stirred at room temperature for 10 min. The mixture was treated with AcOH (12 mL), then concentrated under reduced pressure to a small volume and partitioned between water and CHCl2. The organic phase was washed with water (×2), dried, and filtered through a column of silica gel. The resulting oil was crystallised from EtOAc/petroleum ether to give 1-(chloromethyl)-9-nitro-1,2-dihydro-3H-benzo[e]indole (136) (1.03 g, 91%) as a red solid: mp 100° C.; 1H NMR [(CD3)2SO] δ 8.07 (dd, J=8.0, 1.1 Hz, 1H), 7.94 (dd, J=7.6, 1.3 Hz, 1H), 7.87 (d, J=8.7H, 1H), 7.21 (t, J=7.8 Hz, 1H), 7.13 (d, J=8.7 Hz, 1H), 6.63 (s, 1H), 3.81-3.71 (m, 1H), 3.71-3.62 (m, 1H), 3.62-3.54 (m, 1H), 3.33-3.25 (m, 2H). Anal. (C13H11ClN2O2) C, H, N.

後処理

  1. concentrationconcentrated under reduced pressure to a small volume
  2. custompartitioned between water and CHCl2
  3. washThe organic phase was washed with water (×2)
  4. customdried
  5. filtrationfiltered through a column of silica gel
  6. customThe resulting oil was crystallised from EtOAc/petroleum ether

出典と根拠

ORDレコード
ord-64565ee67ceb453286903c32591b1f7c
出典データセット
uspto-grants-2010_05
特許番号
US07718688B2

反応ノート

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