Hydrochloric Acid → HCID 89581490, compound

HRID 1501157Notes

Reaction equation

HRID 1501157 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH:8]([C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][N:11]=2)[CH3:9])[CH:2]=1.O.[OH-].[Li+].O1CCCC1.Cl>O.CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH:8]([C:10]2[CH:19]=[CH:18][C:13]([C:14]([OH:16])=[O:15])=[CH:12][N:11]=2)[CH3:9])[CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 89581075HCID 89581075, compound

Product 1

HCID 89581490HCID 89581490, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of methyl 6-(1-(pyridin-3-yloxy)ethyl)nicotinate (600 mg, 2.33 mmol), lithium hydroxide monohydrate (420 mg, 10 mmol), tetrahydrofuran (6 mL), methanol (2 mL) and water (2 mL) was stirred at 20° C. for 4 hours. The mixture was acidified to pH=1 with concentrated hydrochloric acid and then extracted with dichloromethane (10 mL×3). The combined organic phase was separated, dried by sodium sulfate and then filtered. The filtrate was concentrated in vacuo to give 6-(1-(pyridin-3-yloxy)ethyl)nicotinic acid (550 mg, 97%).

Workup

  1. extractionextracted with dichloromethane (10 mL×3)
  2. customThe combined organic phase was separated
  3. dry with materialdried by sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-934e0bc1113247b1bcfcc033bc3147e4
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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