Sodium Hydroxide → 3,3',5,5'-Tetramethylbenzidine

HRID 17784

Reaction equation

HRID 17784 reaction equation
Br[C:2]1[CH:8]=[C:7]([CH3:9])[C:5]([NH2:6])=[C:4]([CH3:10])[CH:3]=1.[OH-].[Na+].C([O-])=O.[Na+]>CCCCCCCCCCCCCCCC[N+](C)(C)C.[Br-].[Pd].O>[CH3:10][C:4]1[CH:3]=[C:2]([C:2]2[CH:8]=[C:7]([CH3:9])[C:5]([NH2:6])=[C:4]([CH3:10])[CH:3]=2)[CH:8]=[C:7]([CH3:9])[C:5]=1[NH2:6]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 905494-Bromo-2,6-xylidineHCID 2723810Sodium Formate

Product 1

HCID 412063,3',5,5'-Tetramethylbenzidine

Reagents, catalysts & solvents 3

HCID 5974Hexadecyltrimethylammonium BromideCatalystHCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Compound 1a was prepared using the procedure described in P. Bamfield and P. M. Quan, Synthesis, 1978, 537 using 4-bromo-2,6-dimethylaniline (10.00 g, 50 mmol), CTAB (2.00 g, 5.5 mmol, 0.11 eq.), 5% palladium on charcoal (0.80 g, 50% paste), sodium hydroxide (21.1 ml, 8.0M, 0.169 mol) and sodium formate (2×3.40 g, 100 mmol, 2 eq.) in water (30 ml).

Sources & evidence

ORD record
ord-cc182d9d04484021af87c82eb45ec3f7
Source dataset
uspto-grants-2010_06
Patent number
US07741240B2

Linked notes

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