3,5-Dimethoxyphenol → 3,5-Dimethoxyaniline

HRID 1005647Notes

Reaction equation

HRID 1005647 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](O)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.CCOC(/[N:17]=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl-].[NH4+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1)[NH2:17]

Participants

6

Reactant 4

HCID 103833,5-DimethoxyphenolHCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 663013,5-DimethoxyanilineYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 g of dry 3,5-dimethoxyphenol was dissolved in 25 mL dry THF and cooled in an ice bath. To this solution was added 2.25 g of diethylazodicarboxylate (DEAD), 6 g of triphenylphosphine and 1 mL of ammonium chloride (NH4Cl). The mixture was stirred for 20 minutes. The mixture was warmed to room temperature and stirred for an additional 30 minutes. Silica gel was added to remove DEAD, triphenylphosphine, and excess ammonia, yielding 3,5-dimethoxyaniline.

Workup

  1. temperaturecooled in an ice bath
  2. stirringstirred for an additional 30 minutes
  3. additionSilica gel was added
  4. customto remove DEAD, triphenylphosphine, and excess ammonia

Sources & evidence

ORD record
ord-1ce3efb2b7c546178ab245875f79349e
Source dataset
uspto-grants-2004_09
Patent number
US06787528B2

Reaction notes

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