HCID 12419118, compound → 1-(4-Aminophenyl)-2-(dimethylamino)ethan-1-ol

HRID 2271652Notes

Reaction equation

HRID 2271652 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1)[OH:5]>C(O)C.[Ni]>[NH2:12][C:9]1[CH:8]=[CH:7][C:6]([CH:4]([OH:5])[CH2:3][N:2]([CH3:1])[CH3:15])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 12419118HCID 12419118, compound

Product 1

HCID 543341-(4-Aminophenyl)-2-(dimethylamino)ethan-1-olYield 151.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A pressure flask was charged with a suspension 2-(dimethylamino)-1-(4-nitrophenyl)ethanol (160 mg, 0.770 mmol) in ethanol (10 mL) and Raney nickel (0.5 mL). The flask was placed on a Parr shaker, purged with H2 (30 psi), and stirred for 4 h. The crude product was filtered through celite, and concentrated to obtain the crude product (210 mg) as an off-white solid: 1H NMR (300 MHz, CDCl3) δ 7.11-7.09 (m, 2H), 6.71-6.69 (m, 2H), 4.61-4.70 (m, 1H), 2.61-2.58 (m, 1H), 2.40-2.32 (m, 1H), 2.31 (s, 3H).

Workup

  1. custompurged with H2 (30 psi)
  2. filtrationThe crude product was filtered through celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8ea16c5ec97f4b619a48709781407251
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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