2-Nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,2-diamine

HRID 2189174Notes

Reaction equation

HRID 2189174 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([B:11]2[O:15][C:14]([CH3:17])([CH3:16])[C:13]([CH3:19])([CH3:18])[O:12]2)[CH:8]=[CH:7][C:5]=1[NH2:6])([O-])=O>CO.[Pd]>[CH3:16][C:14]1([CH3:17])[C:13]([CH3:18])([CH3:19])[O:12][B:11]([C:9]2[CH:10]=[C:4]([NH2:1])[C:5]([NH2:6])=[CH:7][CH:8]=2)[O:15]1

Participants

4

Reactant 1

HCID 162179142-Nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 177502424-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of commercially available 2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (2.0 g, 7.5 mmol) in MeOH (50 mL) was added 10% wet Pd—C (50% water in weight, 200 mg). The reaction mixture was flushed with H2 and hydrogenated at 3.3 bar for 2 h. Upon completion the suspension was filtered through Celite to remove the catalyst. The filtrate was concentrated under reduced pressure to give 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,2-diamine, that was submitted to the next step without further purification.

Workup

  1. customThe reaction mixture was flushed with H2 and hydrogenated at 3.3 bar for 2 h
  2. filtrationUpon completion the suspension was filtered through Celite
  3. customto remove the catalyst
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0122daa4bdd8445f8ac4e31fc3a910ef
Source dataset
uspto-grants-2012_12
Patent number
US08324231B2

Reaction notes

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