2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetamide → 5-oxo-5H-dibenzo[a,d]cyclohepten-2-acetic acid

HRID 972988Notes

Reaction equation

C(Cl)(Cl)Cl.CCCCCC.[CH:11]1[C:21]2[CH:20]=[CH:19][C:18]3[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=3[C:16](=[O:26])[C:15]=2[CH:14]=[CH:13][C:12]=1[CH2:27][C:28](N)=[O:29].CC(C)=[O:33].CCCCCC>>[CH:11]1[C:21]2[CH:20]=[CH:19][C:18]3[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=3[C:16](=[O:26])[C:15]=2[CH:14]=[CH:13][C:12]=1[CH2:27][C:28]([OH:29])=[O:33]

Participants

Reactant 3

HCID 204595902-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetamide

HCID 21585165Chloroform hexane

HCID 21880519Acetone hexane

Product 1

HCID 123988215-oxo-5H-dibenzo[a,d]cyclohepten-2-acetic acid

Procedure

3.0 Gm. of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionamide is refluxed in a mixture of 20 ml. of acetic acid and 30 ml. of concentrated hydrochloric acid for 3 hours. The solution is cooled and poured into water. The mixture is extracted with ethyl acetate and the extract is washed, dried and evaporated to yield 90% of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionic acid., m.p. (chloroform-hexane) 138°-139° C.; m.p. (acetone-hexane) 113°-115° C. Use of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetamide gives a similar yield of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetic acid, m.p. (acetone-hexane) 148°-149.5° C.

Sources & evidence

ORD record: ord-cd64f74a697147c4974cb8e09caa11ef
Source dataset: uspto-grants-1977_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04054579

Reaction notes

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