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

HRID 1894649노트

반응식

HRID 1894649 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

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.).

후처리

  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)

출처 및 근거

ORD 기록
ord-7131c86062094bf28b9c0102f94d4459
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513286B2

반응 노트

불러오는 중…