Hydrochloric Acid → HCID 178496796, compound
Reaction equation
CO[C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][N:9]=[C:8]2[OH:15])=[O:4].Cl.C[NH:18]OC.Cl.C(=O)(O)[O-].[Na+].[O:27]1[CH2:31]CC[CH2:28]1>>[CH3:28][O:27][CH2:31][NH:18][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][N:9]=[C:8]2[OH:15])=[O:4]Participants
Procedure
4-Hydroxyquinazoline-6-carboxylic acid methyl ester (XII-1, 4.0 g) was dissolved in tetrahydrofuran (120 ml), N,O-dimethylhydroxylamine hydrochloride (5.7 g) was added, and 2 mol/L iPrMgCl tetrahydrofuran solution (59 ml) was added dropwise over 30 minutes. After completion of addition, the mixture was stirred for 30 minutes under ice cooling and, after completion of the reaction, 40 ml of 2 mol/L hydrochloric acid was added dropwise. The mixture was neutralized with aqueous saturated sodium bicarbonate solution, and extracted with chloroform, and the organic layer was washed with aqueous sodium chloride solution, and dried over sodium sulfate. After concentration, the crystalline residue was purified by silica gel column chromatography (eluting ethyl acetate: methanol=9:1) to obtain 4-hydroxyquinazoline-6-carboxylic acid methoxymethylamide (XIII-1, 2.9 g) as a white solid.
Workup
- additionAfter completion of addition
- additionwas added dropwise
- extractionextracted with chloroform
- washthe organic layer was washed with aqueous sodium chloride solution
- dry with materialdried over sodium sulfate
- concentrationAfter concentration
- customthe crystalline residue was purified by silica gel column chromatography (eluting ethyl acetate: methanol=9:1)
Sources & evidence
- ORD record
- ord-679eb94d37e3477abadca4b6d4be2d26
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08349857B2
Reaction notes
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