Lithium hydroxide, monohydrate → 3-(2-Flourobenzyl)-4-oxo-3,4-dihydroquinazoline-7-carboxylic acid

HRID 1094734Notes

Reaction equation

HRID 1094734 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][C:10]([C:16]([O:18]C)=[O:17])=[CH:11][CH:12]=2)[N:7]=[CH:6]1.O[Li].O>C1COCC1.CO.O>[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][C:10]([C:16]([OH:18])=[O:17])=[CH:11][CH:12]=2)[N:7]=[CH:6]1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59842874Methyl 3-(2-flourobenzyl)-4-oxo-3,4-dihydroquinazoline-7-carboylate

Product 1

HCID 598428393-(2-Flourobenzyl)-4-oxo-3,4-dihydroquinazoline-7-carboxylic acidYield 98.4%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Methyl 3-(2-flourobenzyl)-4-oxo-3,4-dihydroquinazoline-7-carboylate 300 mg, 0.92 mmol) was dissolved In a mixture of THF-MeOH—H2O (10 mL-3 mL-3 mL) followed by the addition of LiOH—H2O (200 mg). The mixture was stirred at RT over night. The solvent evaporated and the residue was dissolved in 4 mL of water and then acidified with 2N HCl to pH˜3. The solid was filtered off dried to gave 270 mg 3-(2-flourobenzyl)-4-oxo-3,4-dihydroquinazoline-7-carboxylic acid in 75% yield.

Workup

  1. customThe solvent evaporated
  2. dissolutionthe residue was dissolved in 4 mL of water
  3. filtrationThe solid was filtered off
  4. customdried

Sources & evidence

ORD record
ord-0286bc2666874943930cf4510462f99f
Source dataset
uspto-grants-2012_03
Patent number
US08133998B2

Reaction notes

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