Nitric Acid → 5-Nitro-2,3-dihydro-1H-inden-2-amine sulfate

HRID 497438Notes

Reaction equation

HRID 497438 reaction equation
Cl.[NH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1.[OH:12][S:13]([OH:16])(=[O:15])=[O:14].[N+:17]([O-])([OH:19])=[O:18]>FC(F)(F)C(O)=O>[S:13]([OH:16])([OH:15])(=[O:14])=[O:12].[NH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:17]([O-:19])=[O:18])[CH:9]=2)[CH2:4]1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 1227642-Aminoindan hydrochloride

Product 1

HCID 160838115-Nitro-2,3-dihydro-1H-inden-2-amine sulfate

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Trifluoroacetic acid (60 mL) was charged into a flask, cooled in an ice/water bath, and 2-aminoindane hydrochloride (10.08 g) was added cautiously, followed by H2SO4 (6.0 mL) and HNO3 (3.0 mL). The ice bath was removed, and the mixture was allowed to warm to room temperature and stir for 2 hours. The mixture was then placed in an ice water bath for the slow addition of diethyl ether (300 mL) over 35 minutes. The mixture was stirred at room temperature overnight, then the solids were filtered and dried in vacuo to give 15.43 g of 2-amino-5-nitro-indane sulfate.

Workup

  1. temperaturecooled in an ice/water bath
  2. customThe ice bath was removed
  3. additionThe mixture was then placed in an ice water bath for the slow addition of diethyl ether (300 mL) over 35 minutes
  4. stirringThe mixture was stirred at room temperature overnight
  5. filtrationthe solids were filtered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-d58e289a51f7402bb5c38e2372389bd5
Source dataset
uspto-grants-2005_09
Patent number
US06949575B2

Reaction notes

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