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

HRID 44440
Notes
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Reaction equation

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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 31092794-Benzylidene-2-(2-chloro-phenyl)-4H-oxazol-5-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 110005543-Isoquinolinecarboxylicacid, 1-(2-chlorophenyl)-Yield 35%

Reagents, catalysts & solvents 1

HCID 124181,1,1,2-TetrachloroethaneSolvent2×

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

  1. customThe reaction mixture was quenched by addition of 1 M HCl (50 ml)
  2. additionThen, the mixture was basified by addition of NaOH (1M aqueous solution)
  3. customthe resulted layers were separated
  4. extractionThis aqueous phase was extracted with CH2Cl2
  5. dry with materialdried over MgSO4
  6. 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

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes