Lithium Hydroxide → HCID 58154615, compound

HRID 2359425Notes

Reaction equation

HRID 2359425 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:16]=[CH:15][C:14]3[C:9](=[C:10]([C:17]([O:19]C)=[O:18])[CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:2]=1.[Li+].[OH-]>C1COCC1.O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:16]=[CH:15][C:14]3[C:9](=[C:10]([C:17]([OH:19])=[O:18])[CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58154662HCID 58154662, compound

Product 1

HCID 58154615HCID 58154615, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 2-(pyridin-3-yl)quinazoline-8-carboxylate (3.5 g, 13.2 mmol) and LiOH (0.48 g, 19.8 mmol) in 1:1 THF/H2O (50 mL) was stirred at 50° C. for 2 hours. The solvent was removed in vacuo and water (20 mL) was added. Aqueous solution was adjusted to pH=3 with 1N aqueous hydrochloride solution. The mixture was extracted with ethyl acetate (3×50 mL). The combined organic layers were dried (Na2SO4), concentrated in vacuo, and purified by silica gel column chromatography (2.5% MeOH in CH2Cl2) to obtain 2-(pyridin-3-yl)quinazoline-8-carboxylic acid (3.0 g, 90% yield).

Workup

  1. customThe solvent was removed in vacuo and water (20 mL)
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by silica gel column chromatography (2.5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-cd65c74859a44ca2a4edd72b47e77e28
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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