Hydrochloric Acid → 5-Methylbenzofuran-7-amine

HRID 1474524Notes

Reaction equation

HRID 1474524 reaction equation
C(=[N:14][C:15]1[C:23]2[O:22][CH:21]=[CH:20][C:19]=2[CH:18]=[C:17]([CH3:24])[CH:16]=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl.[OH-].[Na+]>C1COCC1>[CH3:24][C:17]1[CH:16]=[C:15]([NH2:14])[C:23]2[O:22][CH:21]=[CH:20][C:19]=2[CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58492450HCID 58492450, compound

Product 1

HCID 552848275-Methylbenzofuran-7-amineYield 2,980.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzhydrylidene(5-methylbenzofuran-7-yl)amine (17.9 g, 0.57 mmol) was dissolved in THF (150 ml). 5N Hydrochloric acid (50 ml) was added thereto, followed by stirring at room temperature for 2 hours. A 5N aqueous sodium hydroxide solution (40 ml) was added to the reaction mixture, followed by extraction using ethyl acetate. The extract was sequentially washed with an aqueous saturated sodium hydrogen solution and an aqueous saturated sodium chloride solution. The organic layer was dried over magnesium sulfate and concentrated to dryness under reduced pressure. The residue was purified using silica gel column chromatography (n-hexane:ethyl acetate=50:1→10:1). The purified product was concentrated to dryness under reduced pressure, giving a dark brown oily substance of 5-methylbenzofuran-7-ylamine (2.5 g, yield: 30%).

Workup

  1. extractionfollowed by extraction
  2. washThe extract was sequentially washed with an aqueous saturated sodium hydrogen solution
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe residue was purified
  6. concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-e0683e33c7084aa297108eabe2c0c0aa
Source dataset
uspto-grants-2015_04
Patent number
US09018229B2

Reaction notes

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