7-Nitro-1-tetralone → 7-Amino-1,2,3,4-tetrahydronaphthalen-1-one

HRID 2371787Notes

Reaction equation

HRID 2371787 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=[O:14])=[CH:6][CH:5]=1)([O-])=O>[Pt]=O.C(OCC)(=O)C>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=[O:14])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 384457-Nitro-1-tetralone

Product 1

HCID 3271777-Amino-1,2,3,4-tetrahydronaphthalen-1-oneYield 100%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of platinum oxide (1.6 g), 0.1M aqueous ferric chloride (1 ml), 7-nitro-1-tetralone (15.8 g) and ethyl acetate (400 ml) in a hydrogenation bottle was hydrogenated at 3.5 bar for 3 h. The catalyst was removed by filtration through diatomaceous earth with methanol wash and the filtrate was evaporated to give crude 7-amino-1-tetralone (13.2 g, 100%) as a brown solid; NMR (80 MHz, DMSO-d6) 1.76-2.17(m, 2H, CH2), 2.34-2.90(m, 4H, 2XCH2), 5.10 (br s, 2H, NH2), 6.76(dd, 1H, J=8.3, 2.8 Hz), 7.0(d, 1H, J=8.3 Hz), 7.07 (d, 1H, J=2.8 Hz).

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth with methanol
  2. washwash
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-b998fcf027d643f9a099c8e5637d8c2c
Source dataset
uspto-grants-1992_03
Patent number
US05095038

Reaction notes

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