Hydrochloric Acid → 6-(3-Tert-butyl-phenoxy)-5-methyl-pyridin-3-ylamine

HRID 508473ノート

反応式

HRID 508473 の反応式
C(O)C.Cl.[C:5]([C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=1)[O:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([N+:20]([O-])=O)=[CH:15][N:14]=1)([CH3:8])([CH3:7])[CH3:6]>[Fe].O>[C:5]([C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=1)[O:12][C:13]1[N:14]=[CH:15][C:16]([NH2:20])=[CH:17][C:18]=1[CH3:19])([CH3:8])([CH3:6])[CH3:7]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 581533632-(3-Tert-butyl-phenoxy)-3-methyl-5-nitro-pyridine

生成物 1

HCID 550806946-(3-Tert-butyl-phenoxy)-5-methyl-pyridin-3-ylamine収率 54.4%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

A 100 ml two-necked round-bottomed flask equipped with a KPG-stirrer, a thermometer and a reflux condenser is charged with ethanol (50 ml), water (5 ml), iron (1.43 g) and hydrochloric acid 37% (0.2 ml). The reaction mixture is heated at 50° C. 2-(3-tert-Butyl-phenoxy)-3-methyl-5-nitro-pyridine (2.26 g) was added portionwise. The mixture is heated at reflux for 3 hours. After cooling the mixture to 50° C. it is filtered through celite. The filtrate is poured into water (200 ml) and extracted with ethylacetate (2×50 ml). The combined organic layers are washed with brine (100 ml), dried over sodium sulfate, filtered and the solvent is removed in vacuo. Purification by flash chromatography over silica gel with hexane/ethyl acetate 1:1 (v:v) gives 1.10 g of the compound as a brownish solid (MP: 83-84° C.).

後処理

  1. customA 100 ml two-necked round-bottomed flask equipped with a KPG-stirrer
  2. temperatureThe mixture is heated
  3. temperatureat reflux for 3 hours
  4. temperatureAfter cooling the mixture to 50° C. it
  5. filtrationis filtered through celite
  6. additionThe filtrate is poured into water (200 ml)
  7. extractionextracted with ethylacetate (2×50 ml)
  8. washThe combined organic layers are washed with brine (100 ml)
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customthe solvent is removed in vacuo
  12. customPurification by flash chromatography over silica gel with hexane/ethyl acetate 1:1 (v:v)

出典と根拠

ORDレコード
ord-c9292b3ab4a54b4ea7840df56ced2c23
出典データセット
uspto-grants-2015_08
特許番号
US09096525B2

反応ノート

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