Formic Acid → 7-Amino-1,2,3,4-tetrahydronaphthalen-1-one

HRID 1369009Notes

Reaction equation

HRID 1369009 reaction equation
C([O-])=O.[NH4+].C(O)=O.[N+:8]([C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][CH2:16][CH2:17][C:18]2=[O:21])=[CH:13][CH:12]=1)([O-])=O>CO.[Pd]>[NH2:8][C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][CH2:16][CH2:17][C:18]2=[O:21])=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 384457-Nitro-1-tetraloneHCID 2723923Ammonium formate

Product 1

HCID 3271777-Amino-1,2,3,4-tetrahydronaphthalen-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ammonium formate (2 g), Pd/C (5%; 1 g), and formic acid (0.5 g; cat.) were added in that order to a solution of 7-nitro-1-tetralone (1.95 g; 10 mmol) in methanol (50 mL), and the mixture was stirred for 30 minutes. The solution was filtered, and the filtrate was concentrated. The remainder was soaked with methylene chloride (50+25 mL), and the mixture was filtered and concentrated. Yield 1.4 g (88%).

Workup

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate was concentrated
  3. filtrationthe mixture was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-80ac801a9f704ae6bb152caff0c19996
Source dataset
uspto-grants-2003_06
Patent number
US06576657B2

Reaction notes

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