Acetic acid--water (1/1) → Isopropanol hydrochloride

HRID 2393555Notes

Reaction equation

HRID 2393555 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH2:9][NH:10][CH:11]2[CH2:19][C:18]3[C:13](=[CH:14][C:15]([N+:20]([O-])=O)=[CH:16][CH:17]=3)[CH2:12]2)[CH:6]=[CH:7][CH:8]=1.CC(O)=[O:25].O>[Zn]>[CH3:3][CH:8]([OH:25])[CH3:7].[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([CH2:9][NH:10][CH:11]2[CH2:19][C:18]3[C:13](=[CH:14][C:15]([NH2:20])=[CH:16][CH:17]=3)[CH2:12]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 21899381Acetic acid--water (1/1)HCID 23298395HCID 23298395, compound

Product 2

HCID 21912024Isopropanol hydrochlorideHCID 23298442HCID 23298442, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

To 2-((3-chlorophenyl)methyl)amino-6-nitroindane hydrochloride (2.1 g, 6.13 mmol) in 85% AcOH/H2O (40 ml) was added zinc metal (1.6 g, 24.3 mmol). The mixture was stirred for 5 min, filtered through celite, and evaporated to an oil. The oil was dumped into basic water and extracted with chloroform (3×20 ml). The combined extracts were washed with water, dried over MgSO4, filtered and concentrated to an oil. Treatment with IPA/HCl yielded 2-((3-chlorophenyl)methyl)amino-6-aminoindane: (1.5 g, 70%); m.p.>270° C.

Workup

  1. filtrationfiltered through celite
  2. customevaporated to an oil
  3. extractionextracted with chloroform (3×20 ml)
  4. washThe combined extracts were washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-91c1ddecbc2643819245f113a8584ed8
Source dataset
uspto-grants-1998_09
Patent number
US05807886

Reaction notes

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