Hydrochloric Acid → 2-Nitroimipramine

HRID 1901427

반응식

HRID 1901427 반응식
[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][N:7]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH2:15][CH2:14][C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]1=2)[CH3:3].[N+:22]([O-])([OH:24])=[O:23].Cl>C(O)(=O)C>[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14][CH2:15][C:16]2[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]1=2)[CH3:3]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 944Nitric AcidHCID 3696Imipramine

생성물 1

HCID 1960452-Nitroimipramine수율 51.2%

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

반응 조건

온도
18 °C

실험 절차

Imipramine (4a) (1.925 g, 6.87 mmol) was dissolved in 32 mL acetic acid and cooled to 18° C. Concentrated nitric acid (0.79 mL, 13 mmol) in 1.1 mL acetic acid was added dropwise, with stirring, keeping reaction at 17°-18° C., then reaction stirred at that temperature for an additional 20 minutes. The reaction was then poured into 130 mL of 0.15M HCl and washed with Et2O (2×85 mL), the pH was adjusted to 13 with 10N NaOH and extracted with CHCl3 (4×100 mL). The CHCl3 extracts were combined, washed with 85 mL brine, dried over Na2SO4, and solvent removed in vacuo. The residue was purified by column chromatography, eluting with THF/Hex/NH4OH (70/30/0.4) to yield 1.145 g (51%) of the desired 2-nitroimipramine (4b) as a red oil. 1H NMR (200 MHz, CDCl3) d 8.0-7.9 (m, 2H), 7.3-7.0 (m, 5H), 3.9 (t, 2H), 3.2 (s, 4H), 2.3 (t, 2H), 2.1 (s, 6H), 1.7 (p, 2H); mass spec (FAB) (M+H)+ 326.

후처리

  1. customreaction at 17°-18° C.
  2. customreaction
  3. stirringstirred at that temperature for an additional 20 minutes
  4. washwashed with Et2O (2×85 mL)
  5. extractionextracted with CHCl3 (4×100 mL)
  6. washwashed with 85 mL brine
  7. dry with materialdried over Na2SO4, and solvent
  8. customremoved in vacuo
  9. customThe residue was purified by column chromatography
  10. washeluting with THF/Hex/NH4OH (70/30/0.4)

출처 및 근거

ORD 기록
ord-6a8cbe67defb4816a8b1666ba9ef60f7
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05578500

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