Hydrochloric Acid → 5,6,7,8-Tetrahydro-2-naphthylamine

HRID 1439901Notes

Reaction equation

HRID 1439901 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH2:9][CH2:8][CH2:7]2)([O-])=O.Cl.O.[OH-].[Na+]>CO.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH2:9][CH2:8][CH2:7]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 880181,2,3,4-Tetrahydro-6-nitronaphthalene

Product 1

HCID 751935,6,7,8-Tetrahydro-2-naphthylamineYield 98.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-nitrotetralin (11.5 g, 64.9 mmol) in a mixture of methanol (30 mL) and conc. HCl (40 mL) was added iron powder (11.35 g, 203.2 mmol) by portions over 1 h at room temperature. The mixture was stirred for 1 h at room temperature, poured into water (600 mL), neutralized to ca. pH 6 by addition of 1N aqueous sodium hydroxide, extracted with ethyl acetate (300 mL×2). Organic layers were washed with brine, dried over magnesium sulfate, and concentrated to give 9.45 g of the title compound: 1H NMR (CDCl3) δ6.85 (d, 1H, J=8.1 Hz), 6.46 (dd, 1H, J=8.1, 2.5 Hz), 6.42 (s, 1H), 3.44 (bs, 2H), 2.65 (m, 4H), 1.75 (m, 4H).

Workup

  1. extractionextracted with ethyl acetate (300 mL×2)
  2. washOrganic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d91076b6d30542abab76af1943da1787
Source dataset
uspto-grants-1996_03
Patent number
US05496843

Reaction notes

Loading…