Sodium Hydroxide → HCID 58764155, compound

HRID 859624Notes

Reaction equation

HRID 859624 reaction equation
P(Br)(Br)Br.[Br:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]([CH2:14][CH3:15])[N+:7]=1[O-].[OH-].[Na+]>C(Cl)Cl>[Br:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]([CH2:14][CH3:15])[N:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24614Phosphorus tribromideHCID 86223875HCID 86223875, compound

Product 1

HCID 58764155HCID 58764155, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Phosphorous tribromide (1.3 mL) was added to a solution of 2-bromo-6-ethyl-3-methoxy-pyridine 1-oxide (0.3 g, 1.3 mmol, from step 4 of example A(2)) dissolved in CH2Cl2 (10 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 (0.28 g, 99%). 1H NMR (400 MHz, CDCl3): δ 1.27 (t, J=7.6 Hz, 3 H), 2.76 (d, J=7.6 Hz, 2 H), 3.89 (s, 3 H), 7.06 (d, J=8.1 Hz, 1 H), 7.09 (d, J=8.1 Hz, 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 (0.28 g, 99%)

Sources & evidence

ORD record
ord-67c1c2950c624831a949b78050f4a3a8
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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