Phosphorus oxychloride → 953045-41-5

HRID 335145Notes

Reaction equation

HRID 335145 reaction equation
O=P(Cl)(Cl)[Cl:3].[N+:6]1([O-])[CH:11]=[CH:10][CH:9]=[C:8]2[CH2:12][N:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:14][C:7]=12>>[Cl:3][C:9]1[CH:10]=[CH:11][N:6]=[C:7]2[CH2:14][N:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:12][C:8]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 66995055ethyl 5H-pyrrolo[3,4-b]pyridine-6(7H)-carboxylate N-oxide

Product 1

HCID 66995010953045-41-5Yield 46%

Conditions

Temperature
50 °C

Procedure

POCl3 (20 mL, 218 mmol) was added into ethyl 5H-pyrrolo[3,4-b]pyridine-6(7H)-carboxylate N-oxide (1 g, 4.80 mmol) and heated to 35° C. for 12 hours and 50° C. for another 5 hours. The solvent was evaporated and poured into water. The material was extracted with CH2Cl2, washed with NaHCO3 and brine, dried with Na2SO4, filtered and concentrated. The residue was purified on silica gel to afford the title compound (0.5 g, 45.9% yield).

Workup

  1. customThe solvent was evaporated
  2. additionpoured into water
  3. extractionThe material was extracted with CH2Cl2
  4. washwashed with NaHCO3 and brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-d5c7899da1e948f488341aaf6d922dce
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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