Potassium Nitrate → 5-Nitro-indan-2-ylamine hydrochloride

HRID 2393546Notes

Reaction equation

HRID 2393546 reaction equation
[ClH:1].[NH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1.[N+:12]([O-])([O-:14])=[O:13].[K+]>S(=O)(=O)(O)O>[ClH:1].[N+:12]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[CH2:11][CH:3]([NH2:2])[CH2:4]2)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 1227642-Aminoindan hydrochloride

Product 1

HCID 223193245-Nitro-indan-2-ylamine hydrochloride

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To 2-aminoindane hydrochloride (19.11 g, 0.112 mol) at 0° C. was added sulfuric acid (60 ml) followed by potassium nitrate (11.84 g, 0.117 mol). The mixture was allowed to warm to room temperature, stirred for an additional 2 hr, then dumped onto ice/50% NaOH (500 ml total). The mixture was extracted with ether (3×20 ml) and the combined extracts were washed with water, dried over magnesium sulfate, filtered, and concentrated to an oil which was converted to the hydrochloride salt. Recrystallization from isopropanol/methanol afforded 5-nitro-2-aminoindane hydrochloride: (14.58 g, 60%); m.p. >300° C.

Workup

  1. extractionThe mixture was extracted with ether (3×20 ml)
  2. washthe combined extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to an oil which
  6. customRecrystallization from isopropanol/methanol

Sources & evidence

ORD record
ord-13d411c4d3694f8f90907a406030bf36
Source dataset
uspto-grants-1998_09
Patent number
US05807886

Reaction notes

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