Lithium hydroxide, monohydrate → HCID 70984088, compound

HRID 338849Notes

Reaction equation

HRID 338849 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[C:12](/[CH:15]=[N:16]/[NH:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][N:19]=1)[CH:11]=[CH:10]2)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.C1COCC1.O.O[Li].O>C(Cl)Cl>[C:1]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[C:12]([C:15]1[N:19]3[CH:20]=[C:21]([C:22]([OH:24])=[O:23])[CH:26]=[CH:27][C:18]3=[N:17][N:16]=1)[CH:11]=[CH:10]2)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 168937Lithium hydroxide, monohydrateHCID 12217721Iodo benzene diacetateHCID 21881883Oxolane--water (1/1)HCID 70983754methyl 6-[(2E)-2-[(8-tert-butylquinolin-2-yl)methylidene]hydrazinyl]pyridine-3-carboxylate

Product 1

HCID 70984088HCID 70984088, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (E)-methyl 6-(2-((8-tert-butylquinolin-2-yl)methylene)hydrazinyl)nicotinate (1.78 g, 4.91 mmol) in DCM (40 mL) was added iodobenzene diacetate (1.90 g, 5.89 mmol). The reaction mixture was stirred at ambient temperature for 4 hours. The solvent was removed, and the resulting residue was suspended in 1:1 hexane/ether (50 mL) and stirred at ambient temperature for 10 minutes. The solid that formed was collected by filtration. The solid was then suspended in 1:1 THF/H2O (50 mL) and LiOH—H2O (0.82 g, 19.6 mmol) was added. The reaction mixture was stirred at ambient temperature for 2 hours. THF was removed under reduced pressure. The resulting aqueous solution was acidified with saturated potassium hydrogen sulfate to pH˜3-4. The solid that formed was collected by filtration, washed with water, 1:1 hexane/ether (50 mL) and dried to give 3-(8-tert-butylquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridine-6-carboxylic acid (1.55 g, 91.1%) as solid.

Workup

  1. customThe solvent was removed
  2. stirringstirred at ambient temperature for 10 minutes
  3. customThe solid that formed
  4. filtrationwas collected by filtration
  5. additionwas added
  6. stirringThe reaction mixture was stirred at ambient temperature for 2 hours
  7. customTHF was removed under reduced pressure
  8. customThe solid that formed
  9. filtrationwas collected by filtration
  10. washwashed with water, 1:1 hexane/ether (50 mL)
  11. customdried

Sources & evidence

ORD record
ord-1e6416a52d9a4e84bab8a3584483cc02
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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