Lithium diisopropylamide → HCID 70048242, compound

HRID 864753Notes

Reaction equation

HRID 864753 reaction equation
C([N-]C(C)C)(C)C.[Li+].[Cl:9][C:10]1[C:11]([O:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[N:12][CH:13]=[C:14]([Cl:16])[CH:15]=1.[C:26](=[O:28])=[O:27].C1COCC1>C1COCC1>[ClH:9].[Cl:9][C:10]1[C:11]([O:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[N:12][CH:13]=[C:14]([Cl:16])[C:15]=1[C:26]([OH:28])=[O:27]

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 53650858HCID 53650858, compoundHCID 86748350HCID 86748350, compound

Product 1

HCID 70048242HCID 70048242, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

A solution of lithium diisopropylamide (6.4 g, 0.06 mol) in THF (100 ml) under nitrogen was cooled to -70° C. and a solution of 3, 5-dichloro-2-[2-(4-morpholinyl) ethoxy]pyridine (13.0 g, 0.047 mol) in THF (10 ml) was added via syringe. The yellow/red solution was stirred for 30 minutes at -70° C. and then was slowly warmed to room temperature. The mixture was poured onto crushed dry ice/THF and upon evaporation of the dry ice the solvent was removed in vacuo. The residue was taken up in dilute ammonium hydroxide and extracted with chloroform (2X). The organic layer was separated and concentrated in vacuo to afford 6.0 g of recovered starting material. The aqueous layer was concentrated in vacuo and 3N HCl was added to the residue. The 15 solution was cooled and a solid was obtained which was collected by filtration. The solid was recrystallized from water to afford 3,5-dichloro-2-[2-(4-morpholinyl)ethoxy]pyridine-4-carboxylic acid hydrochloride as a white solid in 71% yield (based on recovered starting material), m.p. 230°-231° C. (dec.).

Workup

  1. temperaturewas slowly warmed to room temperature
  2. additionThe mixture was poured
  3. customupon evaporation of the dry ice the solvent
  4. customwas removed in vacuo
  5. extractionextracted with chloroform (2X)
  6. customThe organic layer was separated
  7. concentrationconcentrated in vacuo
  8. customto afford 6.0 g
  9. customof recovered
  10. concentrationThe aqueous layer was concentrated in vacuo and 3N HCl
  11. additionwas added to the residue
  12. temperatureThe 15 solution was cooled
  13. customa solid was obtained which
  14. filtrationwas collected by filtration
  15. customThe solid was recrystallized from water

Sources & evidence

ORD record
ord-c5842266d2e945e983330692d24f918e
Source dataset
uspto-grants-1996_10
Patent number
US05563163

Reaction notes

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