8-[3-Bromo-4-(2-chloro-4-nitrophenoxy)-2,5-dimethylphenyl]-8-azabicyclo[4.3.0]-nonan-7,9-dione → 8-[4-(4-Amino-2-chlorophenoxy)-3-bromo-2,5-dimethylphenyl]-8-azabicyclo[4.3.0]-nonan-7,9-dione

HRID 1638756Notes

Reaction equation

HRID 1638756 reaction equation
[Br:1][C:2]1[C:3]([CH3:31])=[C:4]([N:20]2[C:28](=[O:29])[CH:27]3[CH:22]([CH2:23][CH2:24][CH2:25][CH2:26]3)[C:21]2=[O:30])[CH:5]=[C:6]([CH3:19])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=1[Cl:18]>C(OCC)(=O)C>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:7]2[C:6]([CH3:19])=[CH:5][C:4]([N:20]3[C:21](=[O:30])[CH:22]4[CH:27]([CH2:26][CH2:25][CH2:24][CH2:23]4)[C:28]3=[O:29])=[C:3]([CH3:31])[C:2]=2[Br:1])=[C:10]([Cl:18])[CH:11]=1

Participants

3

Reactant 1

HCID 198414688-[3-Bromo-4-(2-chloro-4-nitrophenoxy)-2,5-dimethylphenyl]-8-azabicyclo[4.3.0]-nonan-7,9-dione

Product 1

HCID 198414518-[4-(4-Amino-2-chlorophenoxy)-3-bromo-2,5-dimethylphenyl]-8-azabicyclo[4.3.0]-nonan-7,9-dioneYield 84.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Into a Parr bottle was charged 8-[3-bromo-4-(2-chloro-4-nitrophenoxy)-2,5-dimethylphenyl]-8-azabicyclo[4.3.0]-nonan-7,9-dione (3.45 grams, 6.79 mmol) prepared in Part D and ethyl acetate (100 milliliters). The reaction mixture was purged with nitrogen, 5% platinum on carbon (480 milligrams) was added and the mixture was hydrogenated for 1.5 hours at 40-50 psi hydrogen and room temperature on a rocking Parr hydrogenator. Filtration through celite and concentration under reduced pressure afforded the desired product (2.73 grams, 5.71 mmol, 84%). H'-NMR (CDCl3) 6.93 (br s, 1H), 6.80 (d, J=2 Hz, 1H), 6.33 (m, 2H), 3.45 (br s, 2H), 3.06 (br m, 2H) 2.4-1.2 (m, 14H).

Workup

  1. customThe reaction mixture was purged with nitrogen, 5% platinum on carbon (480 milligrams)
  2. additionwas added
  3. filtrationFiltration
  4. concentrationthrough celite and concentration under reduced pressure

Sources & evidence

ORD record
ord-e73cb6a350934c46a114ea4da85b8e3f
Source dataset
uspto-grants-1989_11
Patent number
US04880838

Reaction notes

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