Diisopropylethylamine → 5-(1-Ethylpyrrolidin-3-yl)oxy-4-cyano-2-nitroaniline

HRID 1064368Notes

Reaction equation

HRID 1064368 reaction equation
[C:1]([C:3]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:6]([NH2:7])=[CH:5][C:4]=1F)#[N:2].[CH2:14]([N:16]1[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17]1)[CH3:15].C(N(C(C)C)CC)(C)C>>[CH2:14]([N:16]1[CH2:20][CH2:19][CH:18]([O:21][C:4]2[C:3]([C:1]#[N:2])=[CH:9][C:8]([N+:10]([O-:12])=[O:11])=[C:6]([CH:5]=2)[NH2:7])[CH2:17]1)[CH3:15]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 982031-Ethyl-3-pyrrolidinolHCID 104197934-Amino-2-fluoro-5-nitrobenzonitrile

Product 1

HCID 222730075-(1-Ethylpyrrolidin-3-yl)oxy-4-cyano-2-nitroanilineYield 40.8%

Conditions

Temperature
140 °C

Procedure

To 183 mg of 4-cyano-3-fluoro-6-nitroaniline (which was synthesized following J. Med. Chem. 1994, 37, 467) and 201 mg of 1-ethyl-3-pyrrolidinol, 0.5 ml of diisopropylethylamine was added and stirred for 3 hours at 140° C. The reaction liquid was cooled to room temperature, and concentrated after addition of chloroform-methanol (1/1). The residue was separated and purified on preparative thin-layer chromatography [Kieselgel™ 60F254, Art.5744 (Merck); chloroform/methanol=4/1] to provide 114 mg of the title compound as a yellow solid.

Workup

  1. customThe reaction liquid
  2. temperaturewas cooled to room temperature
  3. concentrationconcentrated
  4. additionafter addition of chloroform-methanol (1/1)
  5. customThe residue was separated
  6. custompurified on preparative thin-layer chromatography [Kieselgel™ 60F254, Art.5744 (Merck); chloroform/methanol=4/1]

Sources & evidence

ORD record
ord-cff466dfb0c044e8943958c6cccd6981
Source dataset
uspto-grants-2005_11
Patent number
US06969712B2

Reaction notes

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