Hydrochloric Acid → HCID 19700735, compound

HRID 861955Notes

Reaction equation

HRID 861955 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](C=[CH:18][CH:19]=1)[C:5]([CH:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[C:9](=[O:16])[O:8]1)=O.[OH-:20].[Na+].Cl.O>CO.O1CCCC1>[OH:20][CH2:18][C:19]1[C:2]([Cl:1])=[CH:3][CH:4]=[CH:5][C:7]=1[C:11]1[C:10]([C:9]([OH:8])=[O:16])=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 70069449HCID 70069449, compound

Product 1

HCID 19700735HCID 19700735, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

7-(3-Chlorobenzoyl)-furo[3,4-b]pyridin-5-one (4.77 g, 19.4 mmoles) and 0.2N sodium hydroxide (21.4 mmoles) was dissolved in methanol and tetrahydrofuran (100 ml, 1:1). The mixture was heated to 75° C. and stirred for 3 hours and cooled. 1N Hydrochloric acid (20 ml) and water (200 ml) was added to the mixture. The resulting solution was extracted with ethyl acetate and dried over Na2SO4. The solution was filtered and the solvent removed yielding 4.94 g (96.8%) of 2-(hydroxymethyl-3-chlorophenyl)-3-carboxypyridine.

Workup

  1. temperaturecooled
  2. extractionThe resulting solution was extracted with ethyl acetate
  3. dry with materialdried over Na2SO4
  4. filtrationThe solution was filtered
  5. customthe solvent removed

Sources & evidence

ORD record
ord-ebaa5bc673044d7da8df6d0aba2899f9
Source dataset
uspto-grants-1998_02
Patent number
US05716954

Reaction notes

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