4-Benzylidene-2-(2-chloro-phenyl)-4H-oxazol-5-one → 3-Isoquinolinecarboxylicacid, 1-(2-chlorophenyl)-

HRID 44440

Reaction equation

[CH:1](=[C:8]1[C:12](=[O:13])[O:11][C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-]>ClCC(Cl)(Cl)Cl>[Cl:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:10]1[C:7]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:1]=[C:8]([C:12]([OH:11])=[O:13])[N:9]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 22 (12 mmol) in tetrachloroethane was added to the suspension of AlCl3 (36 mmol) in tetrachloroethane (50 ml). The resulting mixture was heated to 60° C. for 1.5 hrs. The reaction mixture was quenched by addition of 1 M HCl (50 ml). Then, the mixture was basified by addition of NaOH (1M aqueous solution), the resulted layers were separated, and the aqueous layer was acidified by HCl (aqueous solution). This aqueous phase was extracted with CH2Cl2, dried over MgSO4 and finally the solvents were removed under reduced pressure, to give 35% yield of the desired product.

Workup

customThe reaction mixture was quenched by addition of 1 M HCl (50 ml)
additionThen, the mixture was basified by addition of NaOH (1M aqueous solution)
customthe resulted layers were separated
extractionThis aqueous phase was extracted with CH2Cl2
dry with materialdried over MgSO4
customfinally the solvents were removed under reduced pressure

Sources & evidence

ORD record: ord-35b8cd1e5e834e47815816d05cce98c3
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541428B2

Linked notes

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