Acetic acid--water (1/1) → HCID 23298398, compound

HRID 2393557Notes

Reaction equation

HRID 2393557 reaction equation
Cl.[N+:2]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][CH:11]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=3)[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:23].[NH2:2][C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][CH:11]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=3)[CH2:12]2)=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 21899381Acetic acid--water (1/1)HCID 23298434HCID 23298434, compound

Product 2

HCID 21912024Isopropanol hydrochlorideHCID 23298398HCID 23298398, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

To 7-nitro-2-(((3-chlorophenyl)methyl)amino)1,2,3,4-tetrahydronaphthalene hydrochloride (1.34 g, 3.80 mmol) in 85% AcOH/H2O (75 ml) was added zinc metal (2.48 g, 38.0 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 chcloroform (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-(((3-chlorophenyl)methyl)amino)1,2,3,4-tetrahydronaphthalene (1.4 g, 99%); M.S. (M+H)+ =288.

Workup

  1. filtrationfiltered through celite
  2. customand evaporated to an oil
  3. extractionextracted with chcloroform (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-56bc11943860406c94c527abade2b938
Source dataset
uspto-grants-1998_09
Patent number
US05807886

Reaction notes

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