5-[2-(4-Chlorophenyl)-1,3-dioxolan-2-yl]-3-(3-methoxyphenyl)-2,1-benzisoxazole → (3-Methoxyphenyl)[2-amino-5-[2-(4-chloro-phenyl)-1,3-dioxolan-2-yl]phenyl]methanone

HRID 1636907Notes

Reaction equation

HRID 1636907 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:13]3[CH:14]=[CH:15][C:16]4[C:17]([CH:29]=3)=[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=3)[O:19][N:20]=4)[O:12][CH2:11][CH2:10][O:9]2)=[CH:4][CH:3]=1>C1COCC1.[Pd]>[CH3:28][O:27][C:23]1[CH:22]=[C:21]([C:18]([C:17]2[CH:29]=[C:13]([C:8]3([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[O:12][CH2:11][CH2:10][O:9]3)[CH:14]=[CH:15][C:16]=2[NH2:20])=[O:19])[CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 1

HCID 227143745-[2-(4-Chlorophenyl)-1,3-dioxolan-2-yl]-3-(3-methoxyphenyl)-2,1-benzisoxazole

Product 1

HCID 22714351(3-Methoxyphenyl)[2-amino-5-[2-(4-chloro-phenyl)-1,3-dioxolan-2-yl]phenyl]methanoneYield 103.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Interm. (5-b) (30 g) in THF (250 ml) was hydrogenated with palladium on carbon (3 g) as a catalyst at room temperature for 12 hours under a 2.6 105Pa pressure in a Parr apparatus. After uptake of H2 (1 equivalent), the catalyst was filtered through celite and the filtrate was evaporated till dryness. The product was used without further purification, yielding 31.2 g (100%) of (3-methoxyphenyl)[2-amino-5-[2-(4-chlorophenyl)-1,3-dioxolan-2-yl]phenyl]methanone (interm. 5-c).

Workup

  1. filtrationAfter uptake of H2 (1 equivalent), the catalyst was filtered through celite
  2. customthe filtrate was evaporated till dryness
  3. customThe product was used without further purification

Sources & evidence

ORD record
ord-d5a52ca0edf3418eac8f2d0ffa4d4397
Source dataset
uspto-grants-2000_03
Patent number
US06037350

Reaction notes

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