Sodium Hydroxide → HCID 11784159, compound

HRID 463491Notes

Reaction equation

HRID 463491 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[C:4]([NH2:16])[CH:3]=1.[OH-:17].[Na+]>C1CC=CCCC=C1.C1CC=CCCC=C1.[Ni].O>[NH2:16][C:4]1[CH:3]=[CH:2][C:15]([C:15]2[CH:2]=[CH:3][C:4]([NH2:16])=[C:5]([C:6](=[O:17])[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:14]=2)=[CH:14][C:5]=1[C:6](=[O:7])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 4149946(2-Amino-4-bromophenyl)(phenyl)methanone

Product 1

HCID 11784159HCID 11784159, compound

Reagents, catalysts & solvents 2

HCID 6433264Bis(1,5-cyclooctadiene)nickelCatalystHCID 962WaterSolvent

Procedure

4-Bromo-2-aminobenzophenone (0.55 g, 2.0 mmol) was dissolved in dry and deoxygenated dimethylformamide (10 ml) in an inert atmosphere box. To this was added in portions bis(1,5-cyclooctadiene)nickel (O) (0.55 g, 2.0 mmol). The reaction was moved from the inert atmosphere box to a vacuum-argon manifold using standard Schlenk-wave techniques. The reaction was heated at 5°-55° C. for 4 hrs. and left at room temperature overnight. The mixture was poured into 200 ml of water which was made slightly basic with sodium hydroxide. The water was extracted several times with ethyl acetate which after drying with sodium sulfate and evaporation gave a dark brown liquid (0.48 g). Recrystallization from hexane yielded 100 mg of yellow brown solid mp 180°-185° C.

Workup

  1. customin dry
  2. customdeoxygenated dimethylformamide (10 ml) in an inert atmosphere box
  3. temperatureThe reaction was heated at 5°-55° C. for 4 hrs
  4. extractionThe water was extracted several times with ethyl acetate which
  5. dry with materialafter drying with sodium sulfate and evaporation

Sources & evidence

ORD record
ord-8e497298ec4043ab87ecf999d961fa3f
Source dataset
uspto-grants-1985_05
Patent number
US04519937

Reaction notes

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