Ethanol → 4-Fluoro-3-(morpholin-4-yl)aniline

HRID 1262025ノート

反応式

HRID 1262025 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(O)C.O.O.[Sn](Cl)Cl>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[N:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1

参加物

4

反応物 3

HCID 702EthanolHCID 61436Stannous chloride dihydrateHCID 574160954-(2-Fluoro-5-nitrophenyl)morpholine

生成物 1

HCID 392396264-Fluoro-3-(morpholin-4-yl)aniline収率 80.9%

反応条件

温度
70 °C

実験手順

4-(2-Fluoro-5-nitro-phenyl)-morpholine (335.0 mg, 1.481 mmol) was dissolved in Ethanol (10.0 mL, 171 mmol) and the reaction was treated with Tin(II) chloride dihydrate (1671 mg, 7.405 mmol). The reaction was then heated at 70° C. until HPLC showed consumption of starting material. The mixture was then made basic with 10% NaOH and the product was extracted with ethyl acetate. Note: When adding the NaOH, solid precipitate formed and was filtered and washed with ethyl acetate. The solid was discarded and the combined organics were then washed with water and dried over sodium sulfate, filtered and reduced to afford 235 mg of 4-Fluoro-3-morpholin-4-yl-phenylamine. 1H NMR (400 MHz, DMSO, d6) δ 6.75 (m, 1H), 6.21 (d, 1H, J=7.56 Hz), 6.10 (m, 1H), 4.84 (s, 2H), 3.70 (m, 4H), 2.92 (m, 4H).

後処理

  1. customconsumption of starting material
  2. extractionthe product was extracted with ethyl acetate
  3. additionWhen adding the NaOH, solid precipitate
  4. customformed
  5. filtrationwas filtered
  6. washwashed with ethyl acetate
  7. washthe combined organics were then washed with water
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered

出典と根拠

ORDレコード
ord-1c4d693f8679409e8f854720bb4a01e4
出典データセット
uspto-grants-2013_06
特許番号
US08471005B2

反応ノート

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