Dibenz(c,e)oxepin-5(7H)-one → 2'-Phthalimidomethylbiphenyl-2-carboxylic acid

HRID 2119741Notes

Reaction equation

[CH:1]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[CH2:8][O:7][C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.[K]>CN(C=O)C>[C:17]1(=[O:27])[N:21]([CH2:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[C:11]2[C:5]([C:6]([OH:7])=[O:16])=[CH:4][CH:3]=[CH:2][CH:1]=2)[C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of 35 g (0.17 mol) of 7H-dibenzo[c,e]oxepin-5-one and 30.8 g (0.17 mol) of potassium phthalimide in 330 ml of DMF was heated at 170° C. for 18 h. After cooling, the deposited precipitate was filtered off with suction and introduced into 160 ml of glacial acetic acid. After stirring for 1 h, the mixture was diluted with 650 ml of ice water and the deposited product was filtered off with suction and dried in vacuo. 44.8 g of 2′-phthalimidomethylbiphenyl-2-carboxylic acid were obtained; m.p. 198° C.

Workup

temperatureAfter cooling
filtrationthe deposited precipitate was filtered off with suction
additionintroduced into 160 ml of glacial acetic acid
additionthe mixture was diluted with 650 ml of ice water
filtrationthe deposited product was filtered off with suction
customdried in vacuo

Sources & evidence

ORD record: ord-ae240bb7a6a74f57bab520149a2665d8
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06686395B2

Reaction notes

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