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 42262Notes

Reaction equation

HRID 42262 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>C(OCC)(=O)C.[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 8857Ethyl AcetateSolvent

Procedure

In a 250 mL stainless steel pressure bottle a solution of EXAMPLE 1H (5 g, 18.93 mmol) in ethyl acetate (50 mL) was treated with 10% Pd on carbon (1.25 g, 1.175 mmol). The suspension was stirred under a hydrogen atmosphere for 36 hours at 30 psi at ambient temperature. The mixture was filtered through a nylon membrane and concentrated to provide the title compound. MS APCI(+)) m/e 235.19 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-19a462b379c5474c8c8e41a87a6cd5c8
Source dataset
uspto-grants-2013_09
Patent number
US08536180B2

Reaction notes

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