Acetic acid--water (1/1) → Tetralin

HRID 1953552Notes

Reaction equation

HRID 1953552 reaction equation
[ClH:1].[N+]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][CH:11](N(CC3C=CC=CC=3)C)[CH2:12]2)=[CH:7][CH:6]=1)([O-])=O.CC(O)=[O:26].O>[Zn]>[CH3:6][CH:5]([OH:26])[CH3:14].[ClH:1].[CH2:12]1[C:13]2[C:8](=[CH:7][CH:6]=[CH:5][CH:14]=2)[CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 21899381Acetic acid--water (1/1)HCID 23298435HCID 23298435, 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%); M.S. (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-f822872a90664ca18cc37f068497b636
Source dataset
uspto-grants-2000_09
Patent number
US06117898

Reaction notes

Loading…