Hydrochloric Acid → 1,3-Diisopropyldibenzo[b,d]furan-4-amine

HRID 1750920Notes

Reaction equation

HRID 1750920 reaction equation
[CH:1]([C:4]1[C:12]2[C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[O:9][C:8]=2[C:7]([NH:17]C(=O)C)=[C:6]([CH:21]([CH3:23])[CH3:22])[CH:5]=1)([CH3:3])[CH3:2].Cl.C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH:1]([C:4]1[C:12]2[C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[O:9][C:8]=2[C:7]([NH2:17])=[C:6]([CH:21]([CH3:23])[CH3:22])[CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 58400954N-(1,3-diisopropyldibenzo[b,d]furan-4-yl)acetamide

Product 1

HCID 584009571,3-Diisopropyldibenzo[b,d]furan-4-amineYield 81.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(1,3-diisopropyldibenzo[b,d]furan-4-yl)acetamide (15 g, 48 mmol) was suspended in the mixture of Concentrated HCl (125 mL) and MeOH (125 mL). The mixture 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 1,3-diisopropyldibenzo[b,d]furan-4-amine (10.5 g, 81% yield) as brown solid.

Workup

  1. temperatureThe mixture 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-1b42af9a7a514aa793f76bd68696716b
Source dataset
uspto-grants-2015_10
Patent number
US09156870B2

Reaction notes

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