5-Amino-2-(trifluoromethyl)pyridine → 5-Hydrazinyl-2-(trifluoromethyl)pyridine

HRID 59350

반응식

HRID 59350 반응식
[F:1][C:2]([F:11])([F:10])[C:3]1[N:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[N:12]([O-])=O.[Na+].Cl[Sn]Cl.O>Cl>[NH:9]([C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:10])[F:11])=[N:8][CH:7]=1)[NH2:12]

참가 물질

5

반응물 3

HCID 27377445-Amino-2-(trifluoromethyl)pyridineHCID 23668193Sodium NitriteHCID 43835034Tin dichloride dihydrate

생성물 1

HCID 455981005-Hydrazinyl-2-(trifluoromethyl)pyridine수율 42.7%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매2회

실험 절차

To a cold solution of 6-(trifluoromethyl)pyridin-3-amine (1.5 g, 9.25 mmol) in 4N HCl (60.0 mL) was added aqueous solution of NaNO2 (0.766 g, 11.11 mmol) at 0° C. The reaction mass was stirred at same temperature for 30 minutes. The reaction mass was added to a solution of SnCl2.H2O in 4N HCl at 80° C. and further continued stirring for 5-6 h at same temperature. The reaction mass was cooled, basified and extracted with DCM. The organic layer was dried and concentrated to afford 0.700 g of the product. 1H NMR (300 MHz, DMSO d6): δ 4.29 (br s, 2H), 7.1.8 (dd, J=8.6 Hz, 1H), 7.51 (d, J=8.8 Hz, 1H), 7.68 (s, 1H), 8.13 (d, J=2.4 Hz, 1H); MS (m/z): 178.15 (M+H+).

후처리

  1. stirringfurther continued stirring for 5-6 h at same temperature
  2. temperatureThe reaction mass was cooled
  3. extractionextracted with DCM
  4. customThe organic layer was dried
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a938ea7a7ccc48a984222645edc9262a
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09439890B2

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