Sodium Hydroxide → HCID 22392577, compound

HRID 858655Notes

Reaction equation

HRID 858655 reaction equation
P(Cl)(Cl)Cl.[CH2:5]([C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][N+:8]=1[O-])[CH3:6].[OH-].[Na+]>C(Cl)Cl>[CH2:5]([C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][N:8]=1)[CH3:6]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24387Phosphorus trichlorideHCID 570528HCID 570528, compound

Product 1

HCID 22392577HCID 22392577, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of phosphorous trichloride (7.2 mL, 82 mmol) in CH2Cl2 was added to a cooled 0° C. solution of 2-ethyl-4-nitro-pyridine 1-oxide (3 g, 17.8 mmol) in CH2Cl2. The reaction was stirred for 2 hours and then warmed up to rt. After 3 hours the mixture was poured into ice, made basic with 15% NaOH and extracted with EtOAc. The organic extracts were dried over Na2SO4 and concentrated to a yellow oil that solidified on standing (2.56 g, 95%). 1H NMR (400 MHz, CDCl3): δ 1.40 (t, J=7.6 Hz, 3 H), 3.14 (d, J=7.6 Hz, 2 H), 8.04 (d, J=5.6 Hz, 1 H), 8.06 (s, 1 H), 8.92 (d, J=5.6 Hz, 1 H).

Workup

  1. additionAfter 3 hours the mixture was poured into ice
  2. extractionextracted with EtOAc
  3. dry with materialThe organic extracts were dried over Na2SO4
  4. concentrationconcentrated to a yellow oil that

Sources & evidence

ORD record
ord-9df77be80c03487e815f1bdd81544675
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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