p-Fluoronitrobenzene → HCID 11564737, compound

HRID 734155Notes

Reaction equation

HRID 734155 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[NH2:11][CH:12]([CH2:15][OH:16])[CH2:13][OH:14].C([O-])([O-])=O.[K+].[K+]>CN1CCCC1=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:11][CH:12]([CH2:15][OH:16])[CH2:13][OH:14])=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 68294Serinol

Product 1

HCID 11564737HCID 11564737, compoundYield 3.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

2 g of para-fluoronitrobenzene were added to a solution of 20 ml of N-methylpyrrolidinone, 1.55 g of 2-amino-1,3-propanediol, and 2.35 g of K2CO3. The reaction medium was heated at 60° C. for 15 hours and, after cooling to room temperature, was poured-into a water/ice mixture. A yellow precipitate formed, which was filtered off, reslurried in water, and then dried over P2O5. 0.1 g of 2-(4-nitrophenylamino)propane-1,3-diol (15) was obtained after purification on a column of silica.

Workup

  1. temperatureafter cooling to room temperature
  2. customA yellow precipitate formed
  3. filtrationwhich was filtered off
  4. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-4162ad12421c4f94b6194edfa7e5b3e7
Source dataset
uspto-grants-2009_09
Patent number
US07591860B2

Reaction notes

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