Water → 8,9-dihydro-3-nitro-5H-benzocyclohepten-5-one

HRID 1764720Notes

Reaction equation

C(=O)([O-])[O-].[Li+].[Li+].[Br-].[Li+].[N+:9]([C:12]1[CH:24]=[CH:23][C:15]2[CH2:16][CH2:17][CH2:18][CH:19](Br)[C:20](=[O:21])[C:14]=2[CH:13]=1)([O-:11])=[O:10].O>CN(C)C=O.CCOCC>[N+:9]([C:12]1[CH:24]=[CH:23][C:15]2[CH2:16][CH2:17][CH:18]=[CH:19][C:20](=[O:21])[C:14]=2[CH:13]=1)([O-:11])=[O:10]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 548 g of lithium carbonate and 548 of lithium bromide in 5.480 liters of dimethylformamide was heated to 100° C. and 548 g of 3-nitro-6-bromo-6,7,8,9-tetrahydro [5H] benzocycloheptene-5-one were added thereto over 5 minutes. The mixture was held at 100° C. for 45 minutes and was then poured into 25 liters of a mixture of water and ice. The mixture was vacuum filterd and the insolubles were extracted 8 times with 1 liter of methylene chloride. The organic phase was washed with water, dried over sodium sulfate and was evaporated to dryness under reduced pressure to obtain a red crystalline mass. The latter was empasted successively 3 times with 400 ml of ether, once with 400 ml of ethanol and once with 400 ml of ether and was dried at 40° C. to obtain 286.7 g of 3-nitro-8,9-dihydro [5H] benzocycloheptene-5-one in the form of orange-red crystals melting at 128° C.

Workup

waitThe mixture was held at 100° C. for 45 minutes
extractionthe insolubles were extracted 8 times with 1 liter of methylene chloride
washThe organic phase was washed with water
dry with materialdried over sodium sulfate
customwas evaporated to dryness under reduced pressure
customto obtain a red crystalline mass
dry with materialonce with 400 ml of ethanol and once with 400 ml of ether and was dried at 40° C.

Sources & evidence

ORD record: ord-e25981b1dd0e419b84b93f85781b0263
Source dataset: uspto-grants-1978_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04117164

Reaction notes

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