Hydrochloric Acid → 5-Methylbenzofuran-7-amine

HRID 68136Notes

Reaction equation

HRID 68136 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-16b0765578604f18b887cc78dc92088b
Source dataset
uspto-grants-2014_09
Patent number
USRE045108E1

Reaction notes

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