Sodium Hydroxide → HCID 58764222, compound

HRID 2387010Notes

Reaction equation

HRID 2387010 reaction equation
P(Br)(Br)Br.[Br:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][N+:9]([O-])=[C:8]([CH2:15][CH3:16])[CH:7]=1.[OH-].[Na+]>C(Cl)Cl>[Br:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][N:9]=[C:8]([CH2:15][CH3:16])[CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24614Phosphorus tribromideHCID 67084376HCID 67084376, compound

Product 1

HCID 58764222HCID 58764222, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Phosphorous tribromide (5.5 mL) was added to a solution of 4-bromo-2-ethyl-5-methoxy-pyridine 1-oxide (1.25 g, 5.4 mmol) dissolved in CH2Cl2 (40 mL). The reaction mixture was heated to 50° C. for 1 hour. After cooling to room temperature the mixture was poured into ice and made basic with 15% NaOH and extracted with CH2Cl2. The organic extracts were dried over Na2SO4 and concentrated to a clear oil (1.13 g, 97%). 1H NMR (400 MHz, CDCl3): δ 1.28 (t, J=7.6 Hz, 3 H), 2.75 (q, J=7.6 Hz, 2 H), 3.97 (s, 3 H), 7.37 (s, 1 H), 8.13 (s, 1 H)

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. additionwas poured into ice
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic extracts were dried over Na2SO4
  5. concentrationconcentrated to a clear oil (1.13 g, 97%)

Sources & evidence

ORD record
ord-615a5c58521f4633bb756dd8c7d48dac
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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