4-Nitrophenol → 2-[(Cyclopropylmethyl)aminocarbonyl]-4-(4-nitrophenoxy)pyridine

HRID 387927

Reaction equation

HRID 387927 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][CH2:11][CH:12]2[CH2:14][CH2:13]2)=[O:9])[CH:3]=1.[CH:15]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[C:17]([OH:24])[CH:16]=1.CCN(C(C)C)C(C)C.CN1CCCC1=O>O>[CH:12]1([CH2:11][NH:10][C:8]([C:4]2[CH:3]=[C:2]([O:24][C:17]3[CH:16]=[CH:15][C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=3)[CH:7]=[CH:6][N:5]=2)=[O:9])[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 348291214-Chloro-2-[(cyclopropylmethyl)aminocarbonyl]pyridine

Product 1

HCID 229368972-[(Cyclopropylmethyl)aminocarbonyl]-4-(4-nitrophenoxy)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Chloro-2-[(cyclopropylmethyl)aminocarbonyl]pyridine (1.5 g), p-nitrophenol (2.0 g), Hunig's base (3.1 ml) and 1-methyl-2-pyrrolidinone (6.2 ml) were stirred together at 160° C. for 3 hours. Water was added, extraction was performed with ethyl acetate, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (hexane:ethyl acetate=4:1, followed by 2:1) using NH type silica gel to obtain 0.35 g of the target substance as a colorless oil.

Workup

  1. extractionextraction
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue was purified by column chromatography (hexane:ethyl acetate=4:1, followed by 2:1)
  4. customto obtain 0.35 g of the target substance as a colorless oil

Sources & evidence

ORD record
ord-fbad9ecfc476424d8f3a34685d7a0d78
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Linked notes

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