2-(4-Nitrophenyl)-1,3-dioxolane → 4-(1,3-Dioxolan-2-yl)aniline

HRID 2366333Notes

Reaction equation

HRID 2366333 reaction equation
C(=O)(O)[O-].[Na+].[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[O:19][CH2:18][CH2:17][O:16]2)=[CH:11][CH:10]=1)([O-])=O>CCO.[Pt](=O)=O>[O:16]1[CH2:17][CH2:18][O:19][CH:15]1[C:12]1[CH:13]=[CH:14][C:9]([NH2:6])=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 2667962-(4-Nitrophenyl)-1,3-dioxolaneHCID 516892Sodium Bicarbonate

Product 1

HCID 111266244-(1,3-Dioxolan-2-yl)anilineYield 96.9%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

To a mixture of platinum dioxide (227 mg, 1.00 mmol) and sodium bicarbonate (420 mg, 5.00 mmol) under dry nitrogen was added a solution of 2-(4-nitrophenyl)-1,3-dioxolane (976 mg, 5.00 mmol) in EtOH (30.0 mL). The reaction mixture was bubbled with hydrogen for 15 min and then stirred under a hydrogen atmosphere (balloon) for 2 h. The reaction mixture was then filtered through a pad of Celite washing with MeOH. The filtrate was concentrated under reduced pressure to give the title compound (0.80 g, 96% yield).

Workup

  1. customThe reaction mixture was bubbled with hydrogen for 15 min
  2. filtrationThe reaction mixture was then filtered through a pad of Celite
  3. washwashing with MeOH
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fa24975e9d1f44829f16c35849037786
Source dataset
uspto-grants-2014_04
Patent number
US08697724B2

Reaction notes

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