Hydrochloric Acid → HCID 68227311, compound

HRID 1526631Notes

Reaction equation

HRID 1526631 reaction equation
N[C:2]1[C:6]2=[N:7][CH:8]=[C:9]([Cl:11])[CH:10]=[C:5]2[O:4][C:3]=1C(OCC)=O.Cl.C([O-])(O)=[O:19].[Na+]>>[Cl:11][C:9]1[CH:10]=[C:5]2[O:4][CH2:3][C:2](=[O:19])[C:6]2=[N:7][CH:8]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 90389282HCID 90389282, compound

Product 1

HCID 68227311HCID 68227311, compoundYield 20%

Procedure

A solution of ethyl 3-amino-6-chlorofuro[3,2-b]pyridine-2-carboxylate (0.81 g, 3.35 mmol) in hydrochloric acid (5.0 M in water, 50.0 mL, 3.35 mmol) was heated to reflux for 4 h and cooled to RT. The pH was adjusted to 7 with saturated NaHCO3. The aqueous phase was extracted with EtOAc (3×) and the combined organic extracts were dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel eluting with a gradient of 0% to 100% EtOAc in DCM gave 6-chlorofuro[3,2-b]pyridin-3(2H)-one (0.12 g, 0.68 mmol, 20% yield) as a yellow solid. LC/MS (ESI+) m/z=170.0 (M+H). Calculated for C7H4ClNO2 169.0.

Workup

  1. temperatureto reflux for 4 h
  2. extractionThe aqueous phase was extracted with EtOAc (3×)
  3. dry with materialthe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash column chromatography on silica gel eluting with a gradient of 0% to 100% EtOAc in DCM

Sources & evidence

ORD record
ord-044f28f6fd714496bc12fb51250b1066
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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