Hydrochloric Acid → HCID 68227311, compound

HRID 403246Notes

Reaction equation

HRID 403246 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[O:10][C:9](C(OCC)=O)=[C:8]([OH:16])[C:5]2=[N:6][CH:7]=1.Cl.C([O-])(O)=O.[Na+]>>[Cl:1][C:2]1[CH:3]=[C:4]2[O:10][CH2:9][C:8](=[O:16])[C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68227064HCID 68227064, compound

Product 1

HCID 68227311HCID 68227311, compoundYield 73.2%

Conditions

Temperature
110 °C

Procedure

A mixture of ethyl 6-chloro-3-hydroxyfuro[3,2-b]pyridine-2-carboxylate (154 mg, 637 μmol) and 10% hydrochloric acid (4.65 g, 3.87 ml, 127 mmol) was stirred at 110° C. for 3 hours. To the cooled brown solution was added some ice and neutralized with sat NaHCO3 to pH=8. Then the aqueous layer was extracted thrice with dichloromethane, the combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to give a brown oil. The residue was purified by silica gel flash chromatography with dichloromethane toster) with CH2Cl2 to give the 6-chloro-furo[3,2-b]pyridin-3-one (79 mg, 466 μmol, 73.1% yield) as a light brown solid. MS (ISP): m/z=170.0 [(M+H)+] and 172.0 [(M+2+H)+].

Workup

  1. additionTo the cooled brown solution was added some ice
  2. extractionThen the aqueous layer was extracted thrice with dichloromethane
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a brown oil
  8. customThe residue was purified by silica gel flash chromatography with dichloromethane toster) with CH2Cl2

Sources & evidence

ORD record
ord-b7e4f96828574d91ab2f963079492971
Source dataset
uspto-grants-2014_06
Patent number
US08748418B2

Reaction notes

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