Sulfuric Acid → 4-Fluoro-2-methoxy-5-nitroaniline

HRID 1842690ノート

反応式

HRID 1842690 の反応式
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([O:9][CH3:10])[CH:3]=1.OS(O)(=O)=O.[N+:16]([O-])([O-:18])=[O:17].[K+].[NH4+].[OH-]>>[F:1][C:2]1[C:8]([N+:16]([O-:18])=[O:17])=[CH:7][C:5]([NH2:6])=[C:4]([O:9][CH3:10])[CH:3]=1

参加物

5

反応物 4

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 24434Potassium NitrateHCID 135322284-Fluoro-2-methoxyaniline

生成物 1

HCID 574290724-Fluoro-2-methoxy-5-nitroaniline収率 77.4%

実験手順

4-Fluoro-2-methoxyaniline (2.4 g, 17.00 mmol) was added portionwise to concentrated H2SO4 (15 mL) which was cooled in a ice/water bath, and where the temperature was kept below 15° C. during the addition. The mixture was stirred until all the solid that formed had dissolved. KNO3 (0.815 mL, 17.00 mmol) was added portionwise such that the temperature was maintained below 10° C. The mixture was stirred overnight and then poured onto ice/water. The mixture was basified with concentrated NH4OH. The resulting solid was filtered off and then dissolved in CH2Cl2, washed with water, dried (Na2SO4) and concentrated onto silica. Purification by FCC, eluting with 50-0% heptane in CH2Cl2 gave the title compound (2.450 g, 77%) as a yellow crystalline solid; 1H NMR: 3.91 (3H, s), 5.21 (2H, s), 7.03 (1H, d), 7.35 (1H, d); m/z: ES+ MH+ 187.4.

後処理

  1. temperaturewas cooled in a ice/water bath
  2. additionwhere the temperature was kept below 15° C. during the addition
  3. customthat formed
  4. dissolutionhad dissolved
  5. temperaturewas maintained below 10° C
  6. stirringThe mixture was stirred overnight
  7. additionpoured onto ice/water
  8. filtrationThe resulting solid was filtered off
  9. dissolutiondissolved in CH2Cl2
  10. washwashed with water
  11. dry with materialdried (Na2SO4)
  12. concentrationconcentrated onto silica
  13. customPurification by FCC
  14. washeluting with 50-0% heptane in CH2Cl2

出典と根拠

ORDレコード
ord-e5f5a8e89f9c496787ab527ac1a5a7af
出典データセット
uspto-grants-2015_02
特許番号
US08946235B2

反応ノート

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