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

HRID 1860602Notes

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-13d4c93e10ed4e4d8bc691f2b7318120
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06531495B1

Reaction notes

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