2-Bromophenylhydrazine hydrochloride → HCID 67238175, 화합물

HRID 1623056

반응식

HRID 1623056 반응식
[ClH:1].[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9]N.O=[C:12]1[CH2:18][CH:17]2[N:19](C(OC(C)(C)C)=O)[CH:14]([CH2:15][CH2:16]2)[CH2:13]1>Cl.C(O)(=O)C>[ClH:1].[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[NH:9][C:12]1[CH2:13][CH:14]3[NH:19][CH:17]([C:18]2=1)[CH2:16][CH2:15]3

참가 물질

4

반응물 2

HCID 27239122-Bromophenylhydrazine hydrochlorideHCID 2794767tert-Butyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylate

생성물 1

HCID 67238175HCID 67238175, 화합물

시약·촉매·용매 1

HCID 22641269Acetate-hydrochloric acid용매

반응 조건

온도
22.5 °C

실험 절차

A mixture of 2-bromophenylhydrazine hydrochloride (4.44 g, 19.81 mmol, Aldrich) and t-butyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate (4.48 g, 19.89 mmol, Chem-Impex) in 1 M HCl/acetic acid was stirred at 20-25° C. for 20 hours, and then heated at 65-70° C. for 48 hours. The mixture was cooled to room temperature and concentrated under vacuum. The residue was heated to boiling in absolute ethanol (25 mL) and the suspension was stirred at room temperature for 2 hours, then filtered. The solid was washed with cold ethanol and dried under vacuum to provide the title compound: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.74-1.86 (m, 1H), 2.07 (t, J=9.7 Hz, 1H), 2.15-2.32 (m, 2H), 2.88 (d, J=17.4 Hz, 1H), 3.35-3.49 (m, 1H), 4.41 (s, 1H), 5.16 (d, J=4.4 Hz, 1H), 6.98 (t, J=7.7 Hz, 1H), 7.25-7.37 (m, 1H), 7.58 (d, J=7.9 Hz, 1H), 8.63-9.49 (m, 1H), 11.37 (s, 1H); MS (DCI/NH3) m/z 277/279 (M+H)+.

후처리

  1. temperatureheated at 65-70° C. for 48 hours
  2. temperatureThe mixture was cooled to room temperature
  3. concentrationconcentrated under vacuum
  4. temperatureThe residue was heated
  5. stirringthe suspension was stirred at room temperature for 2 hours
  6. filtrationfiltered
  7. washThe solid was washed with cold ethanol
  8. customdried under vacuum

출처 및 근거

ORD 기록
ord-6cd066fcf4e444b78ea59c84c21acf22
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778959B2

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