[3-(3-Chlorophenyl)-2,1-benzisoxazol-5-yl](4-methylphenyl)-methanone → [2-Amino-5(4-methylbenzoyl)phenyl](3-chlorophenyl)-methanone

HRID 1788058Notes

Reaction equation

HRID 1788058 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][N:10]=[C:11]3[CH:16]=[CH:15][C:14]([C:17]([C:19]4[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=4)=[O:18])=[CH:13][C:12]=23)[CH:5]=[CH:6][CH:7]=1>C1COCC1.O>[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:18])[C:19]2[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=2)=[CH:13][C:12]=1[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)=[O:9]

Participants

4

Reactant 1

HCID 17976102[3-(3-Chlorophenyl)-2,1-benzisoxazol-5-yl](4-methylphenyl)-methanone

Product 1

HCID 17976111[2-Amino-5(4-methylbenzoyl)phenyl](3-chlorophenyl)-methanoneYield 82.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of intermediate 19 (0.071 mol) in THF (250 ml) was cooled on an ice bath. TiCl3 15% in water (250 ml) was added dropwise. The mixture was stirred at room temperature overnight, then poured out into ice water and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated till dryness, yielding 20.5 g (82.6%) of [2-amino-5(4-methylbenzoyl)phenyl](3-chlorophenyl)-methanone (intermediate 20).

Workup

  1. temperaturewas cooled on an ice bath
  2. extractionextracted with DCM
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated till dryness

Sources & evidence

ORD record
ord-af8ca250e0d44d028c48e246ff3d4583
Source dataset
uspto-grants-2009_03
Patent number
US07511138B2

Reaction notes

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