Acetic Acid → HCID 22329052, compound

HRID 586840Notes

Reaction equation

[C:1](O)(=[O:3])C.C(O)=O.[CH2:8]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[CH:19][C:20]3[NH:26][CH2:25][CH2:24][C:23]([C:27]([O:29][CH3:30])=[O:28])=[CH:22][C:21]=3[CH:31]=2)=[CH:13][CH:12]=1)[CH3:9]>C1COCC1>[CH2:8]([O:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:18]=[CH:19][C:20]3[N:26]([CH:1]=[O:3])[CH2:25][CH2:24][C:23]([C:27]([O:29][CH3:30])=[O:28])=[CH:22][C:21]=3[CH:31]=2)=[CH:15][CH:16]=1)[CH3:9]

Participants

Conditions

Temperature: 50 °C

Procedure

To anhydrous acetic acid (0.18 ml) was added dropwise formic acid (0.09 ml) under ice-cooling, and the mixture was stirred under nitrogen atmosphere at 50° C. for 2 hours. To the mixture was added THF (2 ml) and then was added dropwise, under ice-cooling a solution of methyl 7-(4-ethoxyphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.25 g) in THF (15 ml), and the mixture was stirred at room temperature for 4 hours. The solvent was evaporated, and to the residue was added water. The mixture was extracted with ethyl acetate. The organic layer was washed with sodium hydrogen carbonate solution, water and saturated brine, and dried with anhydrous magnesium sulfate, and the solvent was evaporated to give methyl 7-(4-ethoxyphenyl)-1-formyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.24 g) as yellow crystals.

Workup

temperaturecooling
additionwas added dropwise, under ice-
stirringthe mixture was stirred at room temperature for 4 hours
customThe solvent was evaporated
additionto the residue was added water
extractionThe mixture was extracted with ethyl acetate
washThe organic layer was washed with sodium hydrogen carbonate solution, water and saturated brine
dry with materialdried with anhydrous magnesium sulfate
customthe solvent was evaporated

Sources & evidence

ORD record: ord-68a3f36accd645e3b1e7574bcfb91efd
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06936602B1

Reaction notes

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