Acetic acid--water (1/1) → Tetralin

HRID 2393558Notes

Reaction equation

HRID 2393558 reaction equation
[ClH:1].[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.CC(O)=[O:14].O>[Zn]>[CH3:3][CH:2]([OH:14])[CH3:11].[ClH:1].[CH2:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:7][CH2:8][CH2:9]1

Participants

5

Reactant 2

HCID 21899381Acetic acid--water (1/1)HCID 22998565HCID 22998565, compound

Product 2

HCID 8404TetralinHCID 21912024Isopropanol hydrochloride

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

To 7-nitro-2-((phenylmethyl)(methyl)amino)-(1,2,3,4-tetrahydronaphthalene hydrochloride (0.89 g, 2.7 mmol) in 85% AcOH/H2O (75 ml) was added zinc metal (3.5 g, 54.0 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 7-amino-2-((phenyl)methyl)(methyl)amino)-1,2,3,4-tetrahydronaphthalene: (0.81 g, 88%); MS. (M+H)+ =267.

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-af5536d422c34f44b955922d870592a9
Source dataset
uspto-grants-1998_09
Patent number
US05807886

Reaction notes

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