Triethylamine → [2-Amino-5-(2-methyl-1,3-dioxolan-2-yl)phenyl](phenyl)methanone

HRID 463497Notes

Reaction equation

HRID 463497 reaction equation
[CH3:1][C:2]1([C:7]2[CH:8]=[CH:9][C:10]3[C:11]([CH:21]=2)=[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:13][N:14]=3)[O:6][CH2:5][CH2:4][O:3]1.C(N(CC)CC)C>[Pd].O1CCCC1>[NH2:14][C:10]1[CH:9]=[CH:8][C:7]([C:2]2([CH3:1])[O:3][CH2:4][CH2:5][O:6]2)=[CH:21][C:11]=1[C:12]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:13]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 6497105-(2-Methyl-1,3-dioxolan-2-yl)-3-phenyl-2,1-benzoxazole

Product 1

HCID 21828105[2-Amino-5-(2-methyl-1,3-dioxolan-2-yl)phenyl](phenyl)methanoneYield 89.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5-(2-Methyl-1,3-dioxolan-2yl)-3-phenyl-2,1-benzisoxazole (1.50 g, 5.3 m mol), triethyl amine (0.3 ml) and 5% palladium on carbon (0.15 g) were combined in dry tetrahydrofuran (13 ml). The apparatus wa flushed with nitrogen and then hydrogen. A static hydrogen atmosphere was maintained (1 atm.) and the progress of the reaction followed by gas chromatography. The starting material and product have retention times of 11.15 and 11.33 min. respectively. When conversion was complete, the mixture was filtered through a pad of Celite to yield a clear yellow solution. Evaporation of the solution yielded a yellow solid (1.35 g) of mp. 108°-111° C.

Workup

  1. customThe apparatus wa flushed with nitrogen
  2. temperatureA static hydrogen atmosphere was maintained (1 atm.)
  3. customretention times of 11.15 and 11.33 min.
  4. filtrationthe mixture was filtered through a pad of Celite
  5. customto yield a clear yellow solution
  6. customEvaporation of the solution

Sources & evidence

ORD record
ord-c9e8a1bebfb04e5c85a7b72d5c14d392
Source dataset
uspto-grants-1985_05
Patent number
US04519938

Reaction notes

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