Tetrahydrofuran → 2-Butyroylamino-4-(4-nitrophenoxy)pyridine

HRID 1010323Notes

Reaction equation

HRID 1010323 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[NH2:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[CH:11]=[CH:10][N:9]=1.C(N(CC)CC)C.O1CCCC1>O>[C:1]([NH:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=2)[CH:11]=[CH:10][N:9]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 229367164-(4-Nitrophenoxy)pyridin-2-amine

Product 1

HCID 229366772-Butyroylamino-4-(4-nitrophenoxy)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Butyroyl chloride (0.93 ml) was added dropwise to a stirred solution of 2-amino-4-(4-nitrophenoxy)pyridine (1.0 g), triethylamine (1.8 ml) and tetrahydrofuran (20 ml) at room temperature. After stirring for 1 hour, water was added, extraction was performed with ethyl acetate, the extract was dried over magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1) to obtain 0.6 g of the target substance as a colorless oil.

Workup

  1. extractionextraction
  2. dry with materialthe extract was dried over magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1)
  5. customto obtain 0.6 g of the target substance as a colorless oil

Sources & evidence

ORD record
ord-72be4adad6f54b20b7edb3a3c58c8fe7
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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