Water → HCID 59405021, compound

HRID 2387974Notes

Reaction equation

[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:11]=[CH:12][C:6]=2[C:5](=[O:17])[CH:4](C(OC)=O)[CH2:3]1.O>CN1C(=O)CCC1>[F:16][C:13]([F:14])([F:15])[C:10]1[CH:11]=[CH:12][C:6]2[C:5](=[O:17])[CH2:4][CH2:3][C:2](=[O:1])[NH:8][C:7]=2[CH:9]=1

Participants

Conditions

Temperature: 135 °C

Procedure

A 22 L reactor was charged with a solution of methyl 2,5-dioxo-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-4-carboxylate [670 g, 2.22 mol] in NMP (4 L, 6 vol). Water (67 mL, 0.1 vol) was added and the resulting solution was slowly heated to 135° C. The reaction was continued for 15 h when HPLC analysis indicated >99% conversion. The reaction was cooled to ambient temperature. Water (8.7 L, 13 vol) was added slowly with vigorous stirring resulting in a suspension. The suspension was stirred at ambient temperature overnight. The solid was collected by filtration and the filter cake was washed with water (1.5 L). The solid was dried to a constant weight in a vacuum oven at 45° C. to obtain 8-(trifluoromethyl)-3,4-dihydro-1H-1-benzazepine-2,5-dione (522 g, 97% recovery) as an off-white solid. 1H NMR (500 MHz, DMSO-d6) δ ppm: 10.28 (s, 1H), 8.00 (d, 1H, J=8.0 Hz), 7.54 (s, 1H), 7.50 (d, 1H, J=8.0 Hz), 3.00-2.94 (m, 2H), 2.78-2.70 (m, 2H); ESI-MS m/z: 244 (M+H, 100%).

Workup

temperatureThe reaction was cooled to ambient temperature
customresulting in a suspension
stirringThe suspension was stirred at ambient temperature overnight
filtrationThe solid was collected by filtration
washthe filter cake was washed with water (1.5 L)
customThe solid was dried to a constant weight in a vacuum oven at 45° C.

Sources & evidence

ORD record: ord-aae36581548a46409ffb5dc75077bb10
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268992B2

Reaction notes

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