Methyl iodide → HCID 59442751, compound

HRID 1746161Notes

Reaction equation

HRID 1746161 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[NH:14][CH:15]([CH3:17])[CH3:16])([CH3:3])[CH3:2].[H-].[Na+].[CH3:20]I>CN(C=O)C>[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[N:14]([CH:15]([CH3:17])[CH3:16])[CH3:20])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59442723HCID 59442723, compound

Product 1

HCID 59442751HCID 59442751, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2-Isopropoxy-N-isopropyl-5-nitrobenzenamine 29 (218 mg, 0.915 mmol, 1 equiv) in DMF (4 mL) under nitrogen gas, was cooled to 0° C. Sodium hydride (60% oil, 168 mg, 3.84 mmol, 4.2 equiv) was added in one portion, and the reaction mixture was stirred for 10 minutes at 0° C. Methyl iodide (525 uL, 7.68 mmol, 8.4 equiv) was added at 0° C., then the reaction mixture was stirred at ambient temperature for 2 hours, and heated at 80° C. overnight. The reaction mixture was concentrated to dryness and directly loaded into a silica gel flash column and eluted with dichloromethane to provide 2-isopropoxy-N-isopropyl-N-methyl-5-nitrobenzenamine 30 (205 mg, 89%) as a solid.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for 2 hours
  2. temperatureheated at 80° C. overnight
  3. concentrationThe reaction mixture was concentrated to dryness
  4. washeluted with dichloromethane

Sources & evidence

ORD record
ord-42e7c9791b834e19b14d6701863a866e
Source dataset
uspto-grants-2015_10
Patent number
US09149475B2

Reaction notes

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