Sodium Iodide → 4-(2-(Dimethylamino)ethoxy)-2-nitroaniline

HRID 58159

Reaction equation

HRID 58159 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].Cl.Cl[CH2:14][CH2:15][N:16]([CH3:18])[CH3:17].C([O-])([O-])=O.[Cs+].[Cs+].[Na+].[I-]>CC(=O)CC>[CH3:17][N:16]([CH3:18])[CH2:15][CH2:14][O:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 37588824-Amino-3-NitrophenolHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 593493934-(2-(Dimethylamino)ethoxy)-2-nitroanilineYield 45%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 4-amino-3-nitro-phenol (1.54 g, 10 mmol) and (2-chloro-ethyl)-dimethyl-amine hydrogen chloride (1.43 g, 10 mmol) in butanone (40 mL) was added Cs2CO3 (10 g, 30 mmol) and NaI (150 g, 1 mmol). The solution was slowly heated to 80° C. over one hour. Then the solution was stirred at 80° C. for 2 hours. The solution was filtered through Celite® and washed with acetone. The solution was evaporated with silica gel and purified by flash chromatography on silica to afford the title compound (1.0 g, yield: 45%) as a brown solid. 1H-NMR (300 MHz, DMSO-d6) δ 7.38 (d, 1H), 7.24 (s, 2H), 7.16 (dd, 2H), 6.99 (d, 1H), 3.98 (t, 214), 2.58 (t, 2H), 2.20 (s, 6H); MS (ESI) 226 [M+H]+.

Workup

  1. filtrationThe solution was filtered through Celite®
  2. washwashed with acetone
  3. customThe solution was evaporated with silica gel
  4. custompurified by flash chromatography on silica

Sources & evidence

ORD record
ord-d30e336c6ff44153a84cf56115ad7724
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Linked notes

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