Water → HCID 82115337, compound

HRID 1009465Notes

Reaction equation

HRID 1009465 reaction equation
[Cl:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:10](=O)([O-])O.[Na+].Br[CH2:16][CH2:17][C:18]([O:20]C)=[O:19].O>CN(C)P(N(C)C)(N(C)C)=O>[CH3:10][N:5]([C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([Cl:1])[C:3]=1[CH3:9])[CH2:16][CH2:17][C:18]([OH:20])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 68943-Chloro-2-methylanilineHCID 76934Methyl 3-bromopropanoateHCID 516892Sodium Bicarbonate

Product 1

HCID 82115337HCID 82115337, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

1.00 g of 3-chloro-2-methylaniline was dissolved in 10 mL of hexamethylphosphoramide, and 1.80 g of sodium hydrogen carbonate and 1.19 g of methyl 3-bromopropionate sequentially were added thereto, followed by stirring at room temperature for 4 hours. To the reaction liquid was added water, followed by extraction with diisopropyl ether. The organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5 to 85:25) to obtain 0.92 g of methyl N-(3-chloro-2-methylphenyl)-β-alanine.

Workup

  1. customTo the reaction liquid
  2. extractionfollowed by extraction with diisopropyl ether
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5 to 85:25)

Sources & evidence

ORD record
ord-eb07c74021454c2b9a8bbaa981dbc09c
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

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