1,2,3,4-Tetrahydro-6-nitronaphthalene → 5,6,7,8-Tetrahydro-2-naphthylamine

HRID 1615674Notes

Reaction equation

HRID 1615674 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.[N+](C1C=CC=C2C=1CCCC2)([O-])=O.[H][H]>CO.[Pd]>[CH:5]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=[CH:13][C:4]=1[NH2:1]

Participants

6

Reactant 3

HCID 880181,2,3,4-Tetrahydro-6-nitronaphthaleneHCID 931301,2,3,4-Tetrahydro-5-nitronaphthaleneHCID 178418361HCID 178418361, compound

Product 1

HCID 751935,6,7,8-Tetrahydro-2-naphthylamineYield 40%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-nitro-1,2,3,4-tetrahydronaphthalene and 5-nitro-1,2,3,4-tetrahydronaphthalene (5.5 g, 31.1 mmol) in MeOH (50 mL) was added 10% palladium on carbon (3.18 g, 3.0 mmol) under nitrogen, then replaced with hydrogen atmosphere (2 L). The resulting mixture was stirred at room temperature for 16 h, and filtered through Celite. The filtrate was concentrated, and the residue was purified by silica gel column (PE/EtOAc v/v 10:1) to give 5,6,7,8-tetrahydronaphthalen-2-amine as a white solid (2 g, 40% yield). ESI MS: m/z 148 [M+H]+. 1H NMR (400 MHz, CDCl3): δ 6.88 (d, J=8.0 Hz, 1H), 6.49 (dd, J=2.0 Hz, J=8.0 Hz, 1H), 6.44 (d, J=2.0 Hz, 1H), 3.49 (s, 2H), 2.69-2.67 (m, 4H), 1.78-1.75 (m, 4H).

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by silica gel column (PE/EtOAc v/v 10:1)

Sources & evidence

ORD record
ord-bb20b5932f8648d2b156cc61b9972817
Source dataset
uspto-grants-2014_07
Patent number
US08765760B2

Reaction notes

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