Water → 7,8-dimethoxy-3,4-dihydro-1H-1-benzazepine-2,5-dione

HRID 498986Notes

Reaction equation

C(OC([C:6]1[CH2:7][C:8](=[O:22])[NH:9][C:10]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[CH:14][C:11]=2[C:12]=1[OH:13])=O)C.O>CS(C)=O>[CH3:21][O:20][C:15]1[C:16]([O:18][CH3:19])=[CH:17][C:10]2[NH:9][C:8](=[O:22])[CH2:7][CH2:6][C:12](=[O:13])[C:11]=2[CH:14]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A solution of 2,3-dihydro-7,8-dimethoxy-5-hydroxy-2-oxo-1H-[1]-benzazepine-4-carboxylic acid ethyl ester (0.614 g, 1.9 mmol) and water (1 ml) in dimethylsulfoxide (20 ml) was stirred at 150° C. under argon. Portions of water (1 ml) were added after 1 hour and 3 hours heating. After stirring for a total of 6 hours at 150° C., the mixture was cooled to 20° C., poured into ice cold water (20 ml) and allowed to stand overnight at 4° C. The crystals were filtered off and washed with water and hexanes to give the title compound as yellowish crystals (0.325 g, yield 67.7%), mp 230° C.; 1H-NMR (DMSO-d6, 300 MHz): δ (ppm)=8.42 (s; 1H), 7.5 (s; 1H), 6.43 (s; 1H), 3.96 and 3.92 (s; 6H), 2.90 (m, 2H), 2.8 (m; 2H).

Workup

temperatureheating
temperaturethe mixture was cooled to 20° C.
waitto stand overnight at 4° C
filtrationThe crystals were filtered off
washwashed with water and hexanes

Sources & evidence

ORD record: ord-0d97b9e402c5465b8abf21b8fb0e4c42
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767664B2

Reaction notes

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