Ammonium Chloride → 4-Nitro-2,3-dihydro-1H-inden-1-OL

HRID 1434556Notes

Reaction equation

HRID 1434556 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][C:8]2=[O:13])([O-:3])=[O:2].[BH4-].[Na+].[Cl-].[NH4+]>C(O)C>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][CH:8]2[OH:13])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 905634-Nitroindan-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 131024564-Nitro-2,3-dihydro-1H-inden-1-OL

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-nitroindan-1-one (0.381 g, 2.15 mmol) in ethanol (5 ml) was added sodium borohydride (0.048 g, 1.29 mmol) at 0° C., and the mixture was stirred at room temperature for 3 hours. Aqueous solution of ammonium chloride was added to the mixture, and extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to obtain 4-nitroindan-1-ol. 1H NMR (CDCl3) δ 1.90 (d, J=6.5 Hz, 1H), 2.00-2.07 (m, 1H), 2.56-2.63 (m, 1H), 3.25-3.33 (m, 1H), 3.54-3.60 (m, 1H), 5.30-5.35 (m, 1H), 7.44 (t, J=8.2 Hz, 1H), 7.72 (d, J=7.6 Hz, 1H), 8.12 (d, J=8.2 Hz, 1H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6615d58dbf4a4058b4b1fd975ade5427
Source dataset
uspto-grants-2009_11
Patent number
US07615557B2

Reaction notes

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