4-Nitrophenol → HCID 5271203, compound

HRID 544618Notes

Reaction equation

HRID 544618 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[O:13][N:12]=[C:11]([CH3:14])[CH:10]=1.[Na].[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)([O-:18])=[O:17].[I-].[Na+]>O1CCCC1>[CH3:14][C:11]1[CH:10]=[C:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:25][C:22]2[CH:23]=[CH:24][C:19]([N+:16]([O-:18])=[O:17])=[CH:20][CH:21]=2)[O:13][N:12]=1

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 5238Sodium IodideHCID 5360545SodiumHCID 133169675-(7-Bromoheptyl)-3-methylisoxazole

Product 1

HCID 5271203HCID 5271203, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3.0 g (0.0115 mole) of 5-(7-bromoheptyl)-3-methylisoxazole and 1.85 g (0.0115 mole) of the sodium salt of 4-nitrophenol in 50 ml of dry tetrahydrofuran containing a few crystals of sodium iodide was heated at 80° C. for 24 hours. The reaction mixture was concentrated in vacuo and the residue triturated with 100 ml of methylene dichloride and 40 ml of water. The organic phase was dried and concentrated, and the residue crystallized from ether to give 3.5 g of 3-methyl-5-[7-(4-nitrophenoxy)heptyl]isoxazole, colorless solid, m.p. 58° C.; MIC vs. polio-2 virus in vitro=1.5 μg/ml.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue triturated with 100 ml of methylene dichloride and 40 ml of water
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customthe residue crystallized from ether

Sources & evidence

ORD record
ord-91c6f1c159e44bccbcc5be30bd114bcf
Source dataset
uspto-grants-1984_05
Patent number
US04451476

Reaction notes

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