Hydrochloric Acid → 4-Dibenzofuranamine

HRID 1750916Notes

Reaction equation

HRID 1750916 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4]([NH:14]C(=O)C)=[CH:3][CH:2]=1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4]([NH2:14])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 603365HCID 603365, compound

Product 1

HCID 4593514-DibenzofuranamineYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(dibenzo[b,d]furan-4-yl)acetamide (90 g, 400 mmol) was suspended in the mixture of concentrated HCl (240 mL) and methanol (240 mL). The reaction was refluxed for 2 h and then cooled to room temperature. Saturated sodium carbonate was used to neutralize the solution. The residue was collected by filtration and redissolved in DCM. After dried over sodium sulfate, the solution was concentrated to give dibenzo[b,d]furan-4-amine (67 g, 92% yield) as brown solid.

Workup

  1. temperatureThe reaction was refluxed for 2 h
  2. filtrationThe residue was collected by filtration
  3. dissolutionredissolved in DCM
  4. dry with materialAfter dried over sodium sulfate
  5. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-3da70b8dfe19424388ff7ae00b6e089f
Source dataset
uspto-grants-2015_10
Patent number
US09156870B2

Reaction notes

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