Water → HCID 21254723, compound

HRID 2287557Notes

Reaction equation

HRID 2287557 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1.O>CN(C)C=O>[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][O:11][C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=2[NH2:1])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 21254723HCID 21254723, compoundYield 0.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-3-nitrophenol (10 g) in dimethylformamide (100 ml) was added potassium carbonate (17.9 g) under ice-cooling, and the mixture was stirred for 30 minutes at the same temperature. To the mixture was added 4-methoxybenzyl chloride (10.7 g) at ambient temperature, and the mixture was stirred for 30 minutes under ice-cooling and then overnight at ambient temperature. To the reaction mixture was added water, and the mixture was extracted with dichloromethane, and purified by silica gel column chromatography (ethyl acetate-n-hexane). The residue was crystallized with ethanol to give 2-(4-methoxybenzyloxy)-6-nitroaniline (13.6 mg) as yellow needles.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 30 minutes under ice-
  3. temperaturecooling
  4. customovernight
  5. customat ambient temperature
  6. extractionthe mixture was extracted with dichloromethane
  7. custompurified by silica gel column chromatography (ethyl acetate-n-hexane)
  8. customThe residue was crystallized with ethanol

Sources & evidence

ORD record
ord-eb351af4082841b7902eff24dc05c5e1
Source dataset
uspto-grants-2000_07
Patent number
US06083961

Reaction notes

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