Dimethylamine → 5-(Dimethylamino)-2-nitrobenzenemethanol

HRID 1594496Notes

Reaction equation

HRID 1594496 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+]([O-])=O)=[C:6]([CH:11](C2C=CC=CC=2)[OH:12])[C:7]=1[N+:8]([O-:10])=[O:9].ClC1C([N+]([O-])=O)=CC([N+]([O-])=O)=C(C(C2C=CC=CC=2)O)C=1.[CH3:43][NH:44][CH3:45]>CO>[CH3:43][N:44]([CH3:45])[C:4]1[CH:3]=[CH:2][C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH2:11][OH:12])[CH:5]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 86595249HCID 86595249, compoundHCID 86595250HCID 86595250, compound

Product 1

HCID 144593355-(Dimethylamino)-2-nitrobenzenemethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(5-Chloro-2,6-dinitro-phenyl)-phenyl-methanol (13) (0.5 g, 1.90 mmol) or (5-chloro-2,4-dinitro-phenyl)-phenyl-methanol (14) (0.5 g, 2.67 mmol) were treated with 2M solution of dimethylamine in methanol (6 mL) and the solution was heated in a microwave reactor (CEM Focused Microwave™ Synthesis System Model Discover) at 50-55° C. for 15 minutes. The solvent was removed in vacuo and each residue was coevaporated with dichloromethane (2×10 mL) and applied onto a column of silicagel. The column was eluted with dichloromethane/ethanol (49:1) to give compounds 17 and 18.

Workup

  1. temperaturethe solution was heated in a microwave reactor
  2. custom(CEM Focused Microwave™ Synthesis System Model Discover) at 50-55° C. for 15 minutes
  3. customThe solvent was removed in vacuo
  4. washThe column was eluted with dichloromethane/ethanol (49:1)

Sources & evidence

ORD record
ord-97cd06cdbb2545d1a82b631bc86e96ea
Source dataset
uspto-grants-2007_11
Patent number
US07301049B2

Reaction notes

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