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

HRID 508473Notes

Reaction equation

HRID 508473 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

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.).

Workup

  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)

Sources & evidence

ORD record
ord-c9292b3ab4a54b4ea7840df56ced2c23
Source dataset
uspto-grants-2015_08
Patent number
US09096525B2

Reaction notes

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