Methyl iodide → Methyl 4-(allylamino)phenylacetate

HRID 1278307Notes

Reaction equation

HRID 1278307 reaction equation
[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[H-].[Na+].[CH3:17]I>CN(C)P(N(C)C)(N(C)C)=O>[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH3:17])=[O:13])=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 38316Acetic acid, 2-(p-(allylamino)phenyl)-

Product 1

HCID 21163412Methyl 4-(allylamino)phenylacetate

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent2×

Procedure

A solution of 20.7 g. of 4-(allylamino)phenylacetic acid in 25 ml. of hexamethylphosphoramide is added to a stirred mixture of 0.800 g. of sodium hydride (57% in mineral oil) and 25 ml. of hexamethylphosphoramide. The solution which forms after one hour is treated with 11.0 g. of methyl iodide and is then stirred at 25° C. for 18 hours. Dilution with water followed by filtration affords a white solid which is crystallized from ethanol to yield methyl 4-(allylamino)phenylacetate.

Workup

  1. additionis treated with 11.0 g
  2. filtrationDilution with water followed by filtration
  3. customaffords a white solid which
  4. customis crystallized from ethanol

Sources & evidence

ORD record
ord-9d540920e4fc466c9800ed9042b94185
Source dataset
uspto-grants-1981_07
Patent number
US04281019

Reaction notes

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