Acetic Acid → 3-(2,6-Dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine

HRID 425910

반응식

HRID 425910 반응식
CC(O)=O.CCO.[Cl:8][C:9]1[C:25]([F:26])=[CH:24][CH:23]=[C:22]([Cl:27])[C:10]=1[CH2:11][O:12][C:13]1[C:14]([N+:19]([O-])=O)=[N:15][CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Fe].O.C(OCC)C>[Cl:8][C:9]1[C:25]([F:26])=[CH:24][CH:23]=[C:22]([Cl:27])[C:10]=1[CH2:11][O:12][C:13]1[C:14]([NH2:19])=[N:15][CH:16]=[CH:17][CH:18]=1

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 702EthanolHCID 10340Sodium CarbonateHCID 211113993-(2,6-Dichloro-3-fluoro-benzyloxy)-2-nitro-pyridine

생성물 1

HCID 211114003-(2,6-Dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine수율 99%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 962Water용매HCID 3283Diethyl Ether용매

실험 절차

3-(2,6-dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine was prepared following procedure 1. To a stirred mixture of AcOH (650 mL) and EtOH (500 mL) was suspended 3-(2,6-dichloro-3-fluoro-benzyloxy)-2-nitro-pyridine (9.43 g, 0.028 mol) and iron chips (15.7 g, 0.28 mol). The reaction was heated slowly to reflux and allowed to stir for 1 hr. The reaction was cooled to room temperature then diethyl ether (500 mL) and water (500 mL) was added. The solution was carefully neutralized by the addition of sodium carbonate. The combined organic extracts were washed with sat'd NaHCO3 (2×100 mL), H2O (2×100 mL) and brine (1×100 mL) then dried (Na2SO4), filtered and concentrated to dryness under vacuum to yield 3-(2,6-dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine (9.04 g, 0.027 mol, 99%) as a light pink solid. 1H NMR (CDCl3, 300 MHz) δ 1.8-1.85 (d, 3H), 4.9-5.2 (brs, 2H), 6.7-6.84 (q, 1H), 7.0-7.1 (m, 1H), 7.2-7.3 (m, 1H), 7.6-7.7 (m, 1H).

후처리

  1. custom3-(2,6-dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine was prepared
  2. temperatureThe reaction was heated slowly
  3. temperatureto reflux
  4. washThe combined organic extracts were washed with sat'd NaHCO3 (2×100 mL), H2O (2×100 mL) and brine (1×100 mL)
  5. dry with materialthen dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under vacuum

출처 및 근거

ORD 기록
ord-1a79387d940143c6962fe47f4b2e114b
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106197B2

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