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

HRID 1033391Notes

Reaction equation

HRID 1033391 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 (300MHz, CDCl3): 2.09 (m,2H), 2.60 (t,6Hz,2H), 2.84 (t,6Hz,2H), 6.83 (m,1H), 7.06 (d,8Hz,1H), 7.32 (d,2Hz,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-31eec07ac86c4a38b033ac3590dbcf7d
Source dataset
uspto-grants-1994_05
Patent number
US05310737

Reaction notes

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