Sodium Hydroxide → 7-Chlorofuro[2,3-c]pyridine

HRID 564710Notes

Reaction equation

HRID 564710 reaction equation
[O:1]1[C:5]2[C:6](=O)[NH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.CC1C=CC(COC(NNC(C2C=NC=CN=2)=O)=O)=CC=1.[OH-].[Na+].P(Cl)(Cl)([Cl:36])=O>>[Cl:36][C:6]1[N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2][O:1][C:5]=12

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 478568p-tolylmethyl N-(pyrazine-2-carbonylamino)carbamateHCID 12826106Furo[2,3-c]pyridine-7(6H)-one

Product 1

HCID 128261077-Chlorofuro[2,3-c]pyridine

Procedure

A solution of 6-H-furo[2,3-c]pyridin-7-one (1.0 g) in phosphorous oxychloride (10 ml) was stirred at 110° C. for 30 minutes under dry nitrogen. The mixture was cooled, poured onto ice/water (50 ml) and basified to pH10 with 2N sodium hydroxide solution. The mixture was extracted with ether (3×50 ml), the combined extracts dried over sodium sulfate and filtered. Removal of the solvent in vacuo gave the title compound (1.0 g) as a white solid.

Workup

  1. temperatureThe mixture was cooled
  2. additionpoured onto ice/water (50 ml)
  3. extractionThe mixture was extracted with ether (3×50 ml)
  4. dry with materialthe combined extracts dried over sodium sulfate
  5. filtrationfiltered
  6. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-bea149978ea74ce2bb63d0fde5e11375
Source dataset
uspto-grants-2001_01
Patent number
US06169090A

Reaction notes

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