Sulfuric Acid → Isopropanol hydrochloride

HRID 2393550Notes

Reaction equation

HRID 2393550 reaction equation
[NH2:1][CH:2]1[C:10]2[C:5](=CC=CC=2)[CH2:4][CH2:3]1.[ClH:11].[N+:12]([C:15]1[CH:23]=[C:22]2[C:18]([CH2:19][CH2:20][CH:21]2[NH2:24])=[CH:17][CH:16]=1)([O-])=[O:13].[N+]([O-])([O-])=O.[K+].[S:30](=O)(=O)(O)O>>[CH3:3][CH:2]([OH:13])[CH3:10].[ClH:11].[ClH:11].[ClH:11].[NH2:24][CH:21]1[C:22]2[C:18](=[CH:17][CH:16]=[C:15]([NH:12][C:2]([C:3]3[S:30][CH:10]=[CH:5][CH:4]=3)=[NH:1])[CH:23]=2)[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 24434Potassium NitrateHCID 18976283HCID 18976283, compound

Product 2

HCID 21912024Isopropanol hydrochlorideHCID 178478753HCID 178478753, compound

Procedure

6-Nitro-1-aminoindane hydrochloride 1-Aminoindane (10.0 g, 75.08 mmol) was added to concentrated sulfuric acid (40 ml) at 0° C. The mix was warmed to room temperature to aid in solvation then cooled to 0° C. Potassium nitrate (7.60 g, 75.08 mmol) was then added portionwise and the mixture allowed to stir at room temperature for 1 hr before being dumped onto ice/50% NaOH. The aqueous solution was extracted with chloroform (3×100 ml). The combined extracts were washed with water, decolorized with charcoal, dried over magnesium sulfate, filtered, and concentrated to an oil. Treatment with IPA/HCl afforded the sub-titled compound: (6.90 g, 43%); m.p. dec 280° C.

Workup

  1. temperaturethen cooled to 0° C
  2. extractionThe aqueous solution was extracted with chloroform (3×100 ml)
  3. washThe combined extracts were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-9c09f44ff5154e42b9e36fa066b32c65
Source dataset
uspto-grants-1998_09
Patent number
US05807886

Reaction notes

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