3-(7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-on-3-yl)-propionaldehyde diethylacetal → 3-(7,8-dimethoxy-2-oxo-1,2-dihydro-3H-benzo[d]azepin-3-yl)propanal

HRID 648970

Reaction equation

C([O:3][CH:4](OCC)[CH2:5][CH2:6][N:7]1[C:13](=[O:14])[CH2:12][C:11]2[CH:15]=[C:16]([O:21][CH3:22])[C:17]([O:19][CH3:20])=[CH:18][C:10]=2[CH:9]=[CH:8]1)C>S(=O)(=O)(O)O.C(O)C>[CH3:20][O:19][C:17]1[C:16]([O:21][CH3:22])=[CH:15][C:11]2[CH2:12][C:13](=[O:14])[N:7]([CH2:6][CH2:5][CH:4]=[O:3])[CH:8]=[CH:9][C:10]=2[CH:18]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Here, 3-(7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-on-3-yl)-propionaldehyde diethylacetal (3.5 g, 0.01 mol) is heated to 40° C. for 2 hours in 2N sulphuric acid (50 ml) and ethanol (50 ml). The alcohol is distilled off in vacuo, the residue is made alkaline with saturated potassium carbonate solution while cooling and extracted several times with ethyl acetate. The ethyl acetate extract is extracted twice with 5% sodium hydrogen sulfate solution. The bisulphate extract is acidified with concentrated hydrochloric acid and heated to 40° C. in vacuo for half an hour to eliminate the sulphur dioxide. Then saturated potassium carbonate solution is added, the mixture is extracted several times with methylene chloride, dried over magnesium sulphate and concentrated by evaporation.

Workup

distillationThe alcohol is distilled off in vacuo
temperaturewhile cooling
extractionextracted several times with ethyl acetate
extractionThe ethyl acetate extract
extractionis extracted twice with 5% sodium hydrogen sulfate solution
extractionThe bisulphate extract
additionThen saturated potassium carbonate solution is added
extractionthe mixture is extracted several times with methylene chloride
dry with materialdried over magnesium sulphate
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-36540b6089e04859b72fe8cb68eb3645
Source dataset: uspto-grants-1988_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04737495

Linked notes

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