2-Acetoxy-5-nitroindane → 5-Amino-2-acetoxyindane

HRID 267562Notes

Reaction equation

HRID 267562 reaction equation
[C:1]([O:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N+:14]([O-])=O)[CH:11]=2)[CH2:6]1)(=[O:3])[CH3:2]>C(O)C.Cl.O>[NH2:14][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH2:6][CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:13]2

Participants

5

Reactant 1

HCID 224988072-Acetoxy-5-nitroindane

Product 1

HCID 224988125-Amino-2-acetoxyindane

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A slurry of 8.0 g (0.045 moles) of 2-acetoxy-5-nitroindan in 25 ml of absolute ethanol and 32 ml of concentrated hydrochloric acid was treated over 1 hr with a solution of 24 g (0.11 moles) of stannous chloride in 32 ml of absolute ethanol, with water bath cooling to maintain T=20°C. The mixture was stirred for 1 day at room temperature, diluted with 100 ml of water and extracted twice with ether. The aqueous phase was basified with 10% sodium hydroxide until the hydroxides redissolved, then extracted with chloroform, dried (sodium sulfate) and evaporated to an oil which crystallized to 3.9 g (82%) 5-amino-2-hydroxyindan, the hydrochloride of which had mp 237°-239° after one crystallization from ether-methanol isopropanol.

Workup

  1. temperaturecooling
  2. extractionextracted twice with ether
  3. dissolutionredissolved
  4. extractionextracted with chloroform
  5. dry with materialdried (sodium sulfate)
  6. customevaporated to an oil which
  7. customcrystallized to 3.9 g (82%) 5-amino-2-hydroxyindan
  8. customafter one crystallization from ether-methanol isopropanol

Sources & evidence

ORD record
ord-da83f58f363547d5be559489c3fb85fd
Source dataset
uspto-grants-1976_03
Patent number
US03943149

Reaction notes

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