Ammonium formate → 8-Chloro-7-amino-2-(n-propylbenzoyl)amino-1,2,3,4-tetrahydronaphthalene

HRID 266174Notes

Reaction equation

HRID 266174 reaction equation
[Cl:1][C:2]1[C:3]([N+:24]([O-])=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([NH:12][C:13](=[O:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][CH2:21][CH3:22])[CH2:8][CH2:7]2.C([O-])=O.[NH4+]>[Pd]>[Cl:1][C:2]1[C:3]([NH2:24])=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([NH:12][C:13](=[O:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][CH2:21][CH3:22])[CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 190326698-Chloro-7-nitro-2-(n-propylbenzoyl)amino-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 543330228-Chloro-7-amino-2-(n-propylbenzoyl)amino-1,2,3,4-tetrahydronaphthaleneYield 70.9%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 12 g (32 mmol) 8-chloro-7-nitro-2-(n-propylbenzoyl)amino-1,2,3,4-tetrahydronaphthalene, 25 g ammonium formate and 1.0 g Pd/C (added cautiously under inert atmosphere) was stirred over night. After filtering (Celite) and evaporation the material was brought to suspension in ethyl acetate. Filtering and evaporation yielded 7.8 g (22.7 mmol) of 8-chloro-7-amino-2-(n-propylbenzoyl)amino-1,2,3,4-tetrahydronaphthalene, which was recharged with 50 g ammonium formate, 2g Pd/C (added cautiously under inert atmosphere) and 200 ml ethanol. The mixture was stirred at room temperature for 4 days. The reaction ceased at about 1/1 ratio (GLC) of product and starting material. The mixture was worked-up as below and recharged with ammonium formate and Pd/C. After stirring for two days the reaction was almost completed. The mixture was filtered (Celite) and evaporated. Ethyl acetate and water where added, the mixture shaken and separated. The organic phase was washed (10% sodium carbonate),dried (magnesium sulfate), filtered and evaporated to yield 5.3 g (54%) crude product which was purified on silica column (dichloromethane/methanol, 19:1) giving 3.9 g product.

Workup

  1. additionadded cautiously under inert atmosphere)
  2. filtrationAfter filtering
  3. custom(Celite) and evaporation the material
  4. filtrationFiltering
  5. customevaporation

Sources & evidence

ORD record
ord-49709bbb50f5429a84c703aa63782df1
Source dataset
uspto-grants-1997_07
Patent number
US05650427

Reaction notes

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