Sodium Hydroxide → HCID 18387484, compound

HRID 2296615Notes

Reaction equation

HRID 2296615 reaction equation
F[C:2]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:3]=1[CH2:4][N:5]([CH:9]([CH3:11])[CH3:10])[CH2:6][CH2:7][OH:8].[OH-].[Na+]>CS(C)=O.O>[CH:9]([N:5]1[CH2:4][C:3]2[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:2]=2[O:8][CH2:7][CH2:6]1)([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18387473HCID 18387473, compound

Product 1

HCID 18387484HCID 18387484, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To 2-[(2-fluoro-5-nitrobenzyl)(isopropyl)amino]ethanol (31.2 g, 90 mmol) in DMSO (250 ml) was added 25% sodium hydroxide solution (43.2 g, 270 mmol) and the mixture was allowed to stir for 3 h. The reaction was diluted to twice its volume with water and the solids were collected by filtration. The filtrate was extracted with methylene chloride (3×150 ml), washed with water, dried with magnesium sulfate, filtered, and concentrated to an oil. The solid and the oil were dissolved in hot 95% ethanol, then cooled. The solids were collected by filtration (17.47 g, 68%), MS m/z 237 [M+H]+.

Workup

  1. filtrationthe solids were collected by filtration
  2. extractionThe filtrate was extracted with methylene chloride (3×150 ml)
  3. washwashed with water
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. dissolutionThe solid and the oil were dissolved in hot 95% ethanol
  8. temperaturecooled
  9. filtrationThe solids were collected by filtration (17.47 g, 68%), MS m/z 237 [M+H]+

Sources & evidence

ORD record
ord-05754b3b40ac434bbf4a6729770dc1ff
Source dataset
uspto-grants-2002_12
Patent number
US06489322B1

Reaction notes

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