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

HRID 425910

反応式

HRID 425910 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1a79387d940143c6962fe47f4b2e114b
出典データセット
uspto-grants-2012_01
特許番号
US08106197B2

関連ノート

読み込み中…