N-methyl-2-pyrrolidone → HCID 23104615, compound

HRID 734153Notes

Reaction equation

HRID 734153 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].CN1CCCC1=O.[NH2:19][CH:20]([CH2:23][OH:24])[CH2:21][OH:22]>C(N(CC)CC)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:19][CH:20]([CH2:23][OH:24])[CH2:21][OH:22])=[C:3]([CH3:11])[CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-HCID 68294Serinol

Product 1

HCID 23104615HCID 23104615, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

2 g of 2-fluoro-5-nitrotoluene were added to a solution of 20 ml of N-methylpyrrolidinone, 1.4 g of 2-amino-1,3-propanediol, and 1.57 g of triethylamine. The reaction medium was heated at 60° C. for 10 hours and, after cooling to room temperature, was poured into a water/ice mixture. The resulting medium was extracted with ethyl acetate and the organic phase was then concentrated under vacuum. 0.32 g of 2-(4-nitro-2-methylphenylamino)propane-1,3-diol (13) was obtained.

Workup

  1. temperatureafter cooling to room temperature
  2. extractionThe resulting medium was extracted with ethyl acetate
  3. concentrationthe organic phase was then concentrated under vacuum

Sources & evidence

ORD record
ord-c5b963d75c0042c79fd62c852603f52a
Source dataset
uspto-grants-2009_09
Patent number
US07591860B2

Reaction notes

Loading…