N,N-Dimethyl-3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → N1,N1-dimethyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,3-diamine

HRID 1052618Notes

Reaction equation

HRID 1052618 reaction equation
[CH3:1][N:2]([CH3:21])[C:3]1[CH:8]=[C:7]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:6]=[C:5]([N+:18]([O-])=O)[CH:4]=1>C(OCC)(=O)C.[Pd]>[CH3:21][N:2]([CH3:1])[C:3]1[CH:8]=[C:7]([B:9]2[O:10][C:11]([CH3:16])([CH3:17])[C:12]([CH3:15])([CH3:14])[O:13]2)[CH:6]=[C:5]([NH2:18])[CH:4]=1

Participants

4

Reactant 1

HCID 90102809N,N-Dimethyl-3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 131074365N1,N1-dimethyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,3-diamineYield 101.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

N,N-Dimethyl-3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (356 mg, 1.22 mmol) was dissolved in 50 ml of ethyl acetate. This mixture was hydrogenated in an H-Cube® apparatus using 10% palladium on carbon as catalyst at 2-3 bar. The solvent was evaporated to give 324 mg (99% yield) of the title compound as a white solid. Purity 100%.

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-da1c63d64a8e4410bf752346735afa6b
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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