Tetrahydrofuran → 7-Amino-1,2,3,4-tetrahydronaphthalen-1-one

HRID 1591443Notes

Reaction equation

HRID 1591443 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.O1CCCC1>CO.[Pd]>[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

5

Reactant 2

HCID 8028TetrahydrofuranHCID 384457-Nitro-1-tetralone

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

7-Nitrotetralone (2.5 g, 13 mmol) was suspended in 50 mL of methanol and complete dissolution achieved by the addition of 10 mL of tetrahydrofuran. The solution was hydrogenated at room temperature and 20-30 psi over 100 mg of 10% Pd/C for 2 hours. The mixture was filtered through Celite, washed with methanol and evaporated to dryness under vacuum to afford 2.1 g (13 mmol, 100%) of the product. 1H NMR (300 MHz, CDCl3): 2.09 (m,2H), 2.60 (t,6 Hz,2H), 2.84 (t,6 Hz,2H), 6.83 (m,1H), 7.06 (d,8 Hz,1H), 7.32 (d,2 Hz,1H). FAB-MS: calculated for C10H11NO 161; found 162 (M+H,100%).

Workup

  1. dissolutioncomplete dissolution
  2. customwas hydrogenated at room temperature
  3. filtrationThe mixture was filtered through Celite
  4. washwashed with methanol
  5. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-80a2db1dec1c4246959020838d6e5acd
Source dataset
uspto-grants-1993_04
Patent number
US05206235

Reaction notes

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