Acetic Acid → HCID 59303232, 화합물

HRID 2238390노트

반응식

HRID 2238390 반응식
[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

참가 물질

7

반응물 3

HCID 176Acetic AcidHCID 10796Cesium carbonateHCID 44549147HCID 44549147, 화합물

생성물 1

HCID 59303232HCID 59303232, 화합물수율 91.4%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-64565ee67ceb453286903c32591b1f7c
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07718688B2

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