N-methyl-2-pyrrolidone → 2-(4-Nitro-3-methylphenylamino)propane-1,3-diol

HRID 734151Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

2 g of 5-fluoro-2-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. 1.45 g of 2-(4-nitro-3-methylphenylamino)propane-1,3-diol (11) were obtained.

Workup

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

Sources & evidence

ORD record: ord-b590ddcfd94d485c9994ec3f53338e6b
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07591860B2

Reaction notes

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