Methyl iodide → HCID 15735728, compound

HRID 2051239Notes

Reaction equation

HRID 2051239 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:9]([CH:10]([OH:12])[CH3:11])=[CH:8][CH:7]=[CH:6][C:5]=1[NH:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17].[CH3:23]I>CN(C)C=O>[CH3:23][O:17][C:16](=[O:18])[C:15]1[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=1[NH:13][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([CH:10]([OH:12])[CH3:11])[C:4]=1[Cl:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 157357242-[[2-Chloro-3-(1-hydroxyethyl)phenyl]amino]benzoic acid

Product 1

HCID 15735728HCID 15735728, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (0.48 g, 19.9 mmol) is added to a solution of 2-[[2-chloro-3-(1-hydroxyethyl)phenyl]amino]benzoic acid (5.8 g, 19.9 mmol) in dimethylformamide (15 mL) at room temperature. After 15 minutes, the reaction mixture is cooled to 0° C, and methyl iodide (2.8 g, 19.9 mmol) is added dropwise. The reaction mixture is stirred at room temperature overnight, and then partitioned between water and ether. The organic layer is washed with water and brine, dried over magnesium sulfate, and evaporated. Recrystallization of the residue from ether/hexane gives pure 2-[[2-chloro-3-(1-hydroxyethyl)phenyl]amino]benzoic acid methyl ester (4.6 g, 76%), mp=94-95° C.

Workup

  1. custompartitioned between water and ether
  2. washThe organic layer is washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customRecrystallization of the residue from ether/hexane

Sources & evidence

ORD record
ord-6b9c2f58c0704f1082a0696cc443354a
Source dataset
uspto-grants-1991_05
Patent number
US05017604

Reaction notes

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