Hydrochloric Acid → HCID 12957239, compound

HRID 1088438Notes

Reaction equation

HRID 1088438 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH:9](=O)[C:10]1[O:14][CH:13]=[CH:12][CH:11]=1.B.[Na].Cl>C(O)C>[O:14]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH2:9][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 58012-AminophenolHCID 7362FurfuralHCID 178418435HCID 178418435, compound

Product 1

HCID 12957239HCID 12957239, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In 20 ml of ethanol was dissolved 5.0 g (45.8 millimoles) of 2-aminophenol, and 4.8 g (50.0 millimoles) of furfural was added to the solution and the mixture was stirred for 1 hour at room temperature. Then, 2.3 g (60.8 millimoles) of sodium boron hydride was added to the mixture and the mixture was stirred at room temperature for 2 hours, and 2N hydrochloric acid was added to the mixture and ethanol was removed by distillation under reduced pressure. Then, the residue was neutralized with a 5% aqueous solution of sodium hydroxide and extracted with ethyl acetate. The organic layer was dried with sodium sulfate and concentrated under reduced pressure, and the residue was purified by the silica gel column chromatography (developing solvent: ethyl acetate/hexane=3/7) to obtain 5.0 g (the yield was 58%) of 2-(2-furyl)methylaminophenol in the form of a brown oil. The oil was dissolved in 200 ml of an aqueous solution of 2.5 g of sodium hydroxide, and 2.5 ml (30 millimoles) of 1,2-chlorobromoethane was added to the solution and the mixture was heated and refluxed for 5 hours. The reaction mixture was extracted, and the extract was dried with anhydrous sodium sulfate and concentrated under reduced pressure to obtain a brown oil. The oil was purified by the silica gel column chromatography (developing solvent: chloroform/hexane=1/3→1/1) to obtain 0.5 g (the yield was 7.5%) of intended compound No. 11 in the form of a light-brown oil.

Workup

  1. additionwas added to the solution
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. customwas removed by distillation under reduced pressure
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified by the silica gel column chromatography (developing solvent: ethyl acetate/hexane=3/7)

Sources & evidence

ORD record
ord-15cf2783237443368122756ea442df36
Source dataset
uspto-grants-1990_10
Patent number
US04962200

Reaction notes

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