Hydroxyphenylacetic acid → HCID 19082072, compound

HRID 963301Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:24][C:25]1[CH:30]=[CH:29][N:28]=[C:27]([CH2:31][CH3:32])[C:26]=1[Cl:33].O>O1CCOCC1>[Cl:33][C:26]1[C:27]([CH2:31][CH3:32])=[N:28][CH:29]=[CH:30][C:25]=1[NH:24][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 5 °C

Procedure

0.76 g (5.0 mmol) of 4-hydroxyphenyl acetic acid was dissolved in 20 ml of 1,4-dioxane, and the solution was stirred at 5° C. Then, 0.97 g (6.0 mmol) of 1,1'-carbonyldiimidazole was added thereto, and the mixture was stirred for one hour at 5° C. Then, 0.76 g (5.0 mmol) of 4-amino-3-chloro-2-ethylpyridine was added thereto, and the mixture was refluxed under heating for 20 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. Then, ethyl acetate was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) and then recrystallized from ethanol to obtain 0.7 g of the desired product as a white powder (melting point: 158° to 161° C.).

Workup

stirringthe mixture was stirred for one hour at 5° C
temperaturethe mixture was refluxed
temperatureunder heating for 20 hours
extractionextracted with ethyl acetate
washThe organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
distillationThen, ethyl acetate was distilled off under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate)
customrecrystallized from ethanol

Sources & evidence

ORD record: ord-707e8aa56c7b4f38b6827f1eecbc1380
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05763463

Reaction notes

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