Dichloromethane → 2-(Methoxymethyl)-4-nitroaniline

HRID 1472975Notes

Reaction equation

HRID 1472975 reaction equation
[OH:1][CH2:2][C:3]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:4]=1[NH2:5].[OH-].[Na+].S(OC)(O[CH3:19])(=O)=O.ClCCl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[CH3:19][O:1][CH2:2][C:3]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:4]=1[NH2:5]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 30187062-Amino-5-nitrobenzyl alcohol

Product 1

HCID 114011432-(Methoxymethyl)-4-nitroanilineYield 42%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

2-Hydroxymethyl-4-nitroaniline (1.0 g, 5.75 mmol) is suspended in petroleum ether (10 mL). Sodium hydroxide solution (50%, 618 mg, 15.46 mmol) and benzyltriethylammonium chloride (20 mg) are added with stirring. Dimethyl sulfate (728 uL, 7.7 mmol) is added and the reaction mixture is stirred at room temperature for 16 h. Dichloromethane (50 mL) and water (25 mL) are added and the layers are separated. The organic layer is washed with saturated NaHCO3 and evaporated affording 440 mg of 2-methoxymethyl-4-nitroaniline (Ma) in 82% purity.

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 16 h
  2. customthe layers are separated
  3. washThe organic layer is washed with saturated NaHCO3
  4. customevaporated

Sources & evidence

ORD record
ord-ee1ae6631a7642f1a5faff8df5579f0c
Source dataset
uspto-grants-2015_04
Patent number
US09012691B2

Reaction notes

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