Potassium Carbonate → 2-(4,6-Dimethoxy-2-pyrimidinyloxy)benzaldoxime

HRID 344570Notes

Reaction equation

Cl.[NH2:2][OH:3].C(=O)([O-])[O-].[K+].[K+].[CH3:10][O:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[N:15]=[C:14]([O:20][C:21]2[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=2[CH:23]=O)[N:13]=1>O.CO>[CH3:10][O:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[N:15]=[C:14]([O:20][C:21]2[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=2[CH:23]=[N:2][OH:3])[N:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3.5 g of hydroxylamine hydrochloride were added to 100 ml of a 1:1 mixed solution of water and methanol containing 3.5 g of potassium carbonate at 0° C. The solution was stirred at 0° C. for 10 minutes. At 0° C., 13.0 g of 2-(4,6-dimethoxy-2-pyrimidinyloxy)benzaldehyde were added to the reaction mixture. The resulting mixture was stirred at room temperature for 1 hour and then warmed at 60° C. for 1 hour. After the reaction mixture was allowed to cool down, it was poured into water, followed by extraction with ethyl acetate. The organic layer was desired over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel chromatography (developer: n-hexane:ethyl acetate=5:1) to obtain 7.7 g of 2-(4,6-dimethoxy-2-pyrimidinyloxy)benzaldoxime.

Workup

stirringThe resulting mixture was stirred at room temperature for 1 hour
temperaturewarmed at 60° C. for 1 hour
temperatureto cool down
extractionfollowed by extraction with ethyl acetate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography (developer: n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record: ord-7865867b5b3b409680b85909638800ac
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05053070

Reaction notes

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