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

HRID 1433589Notes

Reaction equation

HRID 1433589 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-d04a42bf09534488ad8382976a3d4a7f
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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