5-Bromo-N,3-dimethyl-2-nitrobenzenamine → HCID 69058379, compound

HRID 873941Notes

Reaction equation

HRID 873941 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([N+:10]([O-])=O)=[C:6]([CH:9]=1)[NH:7][CH3:8]>C1COCC1.CO.[Ni]>[Br:1][C:2]1[CH:9]=[C:6]([NH:7][CH3:8])[C:5]([NH2:10])=[C:4]([CH3:13])[CH:3]=1

Participants

5

Reactant 1

HCID 1177027265-Bromo-N,3-dimethyl-2-nitrobenzenamine

Product 1

HCID 69058379HCID 69058379, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-N,3-dimethyl-2-nitroaniline (Step 85.1) (2.7 g, 11.02 mmol) in THF (100 mL) and MeOH (100 mL) was added Raney Nickel (189 mg, 2.203 mmol) and the resulting mixture was stirred under hydrogen atmosphere at RT for 16 hr. The reaction was filtered through a pad of Celite and the resulting filtrate was concentrated under reduced pressure to afford the title product (2.5 g, 10.56 mmol, 96% yield) as off-white solid. tR: 0.94 min (LC-MS 2); ESI-MS: 214 [M+H]+ (LC-MS 2).

Workup

  1. filtrationThe reaction was filtered through a pad of Celite
  2. concentrationthe resulting filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d716443546a24a7e86caefceee819323
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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