HCID 22712342, compound → HCID 22712345, compound

HRID 394576Notes

Reaction equation

HRID 394576 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[C:5]([N+:10]([O-])=O)[C:4]=1[CH3:13]>C1COCC1.[H][H].[Ni]>[Br:9][C:6]1[CH:7]=[CH:8][C:3]([N:2]([CH3:14])[CH3:1])=[C:4]([CH3:13])[C:5]=1[NH2:10]

Participants

5

Reactant 1

HCID 22712342HCID 22712342, compound

Product 1

HCID 22712345HCID 22712345, compoundYield 90.5%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

15 g of N,N-dimethyl-4-bromo-2-methyl-3-nitroaniline is dissolved in about 200 ml of THF and hydrogenated at 20° C. under 5 bars pressure of hydrogen using Raney nickel as catalyst. 12 g of 2-bromo-5-dimethylamino-6-methylaniline is obtained as a brown oil.

Sources & evidence

ORD record
ord-aa39f71d8db04dd4a0d2be9cc84c90e8
Source dataset
uspto-grants-2003_08
Patent number
US06602897B2

Reaction notes

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