Sodium Hydroxide → HCID 68663750, compound

HRID 452629Notes

Reaction equation

HRID 452629 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]2[NH:18][C:12]3=[N+:13]([O-])[CH:14]=[CH:15][CH:16]=[C:11]3[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:21])=O.[OH-].[Na+]>>[Cl:21][C:16]1[CH:15]=[CH:14][N:13]=[C:12]2[NH:18][C:9]([CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:10][C:11]=12

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178526240HCID 178526240, compound

Product 1

HCID 68663750HCID 68663750, compoundYield 56.3%

Procedure

A mixture of 2-(2-phenylethyl)-1H-pyrrolo[2,3-b]pyridine 7-oxide (1.17 g, 4.91 mmol) and phosphorus oxychloride (9.73 g) was heated under reflux for 2 hr. The reaction mixture was poured into ice water, and the mixture was neutralized with sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-0/1) and washed with hexane to give the title compound (0.71 g, yield 56%) as colorless crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hr
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-0/1)
  8. washwashed with hexane

Sources & evidence

ORD record
ord-8af3004fdb43411580488dc8dc791f6c
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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