Ammonium Chloride → 4-amino-2,3-dihydro-1H-inden-2-yl acetate

HRID 1434559

Reaction equation

HRID 1434559 reaction equation
[C:1]([O:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N+:14]([O-])=O)[CH2:6]1)(=[O:3])[CH3:2].[Cl-].[NH4+]>C(O)C.O.C(OC(=O)C)C.[Fe]>[C:1]([O:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH2:14])[CH2:6]1)(=[O:3])[CH3:2]

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 132395834-nitro-2,3-dihydro-1H-inden-2-yl acetate

Product 1

HCID 132395844-amino-2,3-dihydro-1H-inden-2-yl acetate

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 4-nitro-2,3-dihydro-1H-inden-2-yl acetate (100 mg, 0.45 mmol) and ammonium chloride (100 mg) in ethanol (6 ml) and water (3 ml) was added iron powder (300 mg) portionwise at room temperature. The mixture was stirred at 90° C. for 1 hour, and after cooled to room temperature, the mixture was diluted with ethylacetate. The mixture was filtered through a pad of celite, and the filtrate was washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to obtain 4-amino-2,3-dihydro-1H-inden-2-yl acetate.

Workup

  1. temperatureafter cooled to room temperature
  2. filtrationThe mixture was filtered through a pad of celite
  3. washthe filtrate was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-57ffff16dce048048ddc75e42ca245dc
Source dataset
uspto-grants-2009_11
Patent number
US07615557B2

Linked notes

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