4-Nitroindan-1-one → 4-amino-2,3-dihydro-1H-inden-1-one

HRID 1822870Notes

Reaction equation

HRID 1822870 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-])=O>Cl.O>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][C:8]2=[O:13]

Participants

4

Reactant 1

HCID 905634-Nitroindan-1-one

Product 1

HCID 221702144-amino-2,3-dihydro-1H-inden-1-oneYield 90.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

4-Nitro-1-indanone (0.84 g, 4.75 mmol) was suspended in aqueous hydrochloric acid (9 M, 40 ml) and stannous chloride (3 g, 15.8 mmol) was added. The mixture was stirred at ambient temperature. After 2 h a clear solution was obtained. The stirring was continued for 23 h after which time a yellow precipitate had formed. The reaction mixture was diluted with water and washed trice with methylene chloride. The aqueous phase was made alkaline with 2 M aqueous NaOH and extracted four times with methylene chloride. The combined organic phases was washed with water, dried (Na2SO4), filtered, evaporated and finally dried to give the title compound (630 mg, 90%).

Workup

  1. customAfter 2 h a clear solution was obtained
  2. customafter which time a yellow precipitate had formed
  3. washwashed trice with methylene chloride
  4. extractionextracted four times with methylene chloride
  5. washThe combined organic phases was washed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customfinally dried

Sources & evidence

ORD record
ord-5e96fc61cc544e698631b5627e4e3a14
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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