Hexane → 3-(2-Amino-5-chlorobenzoyl)phenyl-1,3-dioxolane

HRID 275842Notes

Reaction equation

HRID 275842 reaction equation
CN(OC)[C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[NH2:11].Br[C:16]1[CH:17]=[C:18]([CH:22]2[O:26][CH2:25][CH2:24][O:23]2)[CH:19]=[CH:20][CH:21]=1.CCCCCC.C([Li])CCC>O1CCCC1.C(OC(=O)C)C.O>[NH2:11][C:5]1[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:4]=1[C:3]([C:20]1[CH:19]=[C:18]([CH:22]2[O:23][CH2:24][CH2:25][O:26]2)[CH:17]=[CH:16][CH:21]=1)=[O:12]

Participants

8

Reactant 4

HCID 8058HexaneHCID 873062-(3-Bromophenyl)-1,3-dioxolaneHCID 222266052-amino-5-chloro-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

Product 1

HCID 179398123-(2-Amino-5-chlorobenzoyl)phenyl-1,3-dioxolaneYield 57.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-methyl-N-methyloxy-2-amino-5-chlorobenzamide (2 g) and 2-(3-bromophenyl)-1,3-dioxolane (2.1 g) in tetrahydrofuran (65 ml) was cooled to −78° C. To the solution was added dropwise gradually a hexane solution of n-butyl lithium (1.6 mol/L)(11.6 ml). To the mixture were added water (300 ml) and acetic acid ethyl ester (50 ml). The organic layer was washed with water and dried over anhydrous Na2SO4, then the solvent was distilled off. The residue was purified by means of a silica gel column chromatography to give 2-[3-(2-amino-5-chlorobenzoyl)phenyl-1,3-dioxolane (1.6 g) as a colorless oily compound.

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over anhydrous Na2SO4
  3. distillationthe solvent was distilled off
  4. customThe residue was purified by means of a silica gel column chromatography

Sources & evidence

ORD record
ord-2cf38538b76d4346b5ad9db66e92fb19
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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