Water → HCID 22708811, compound

HRID 353344Notes

Reaction equation

HRID 353344 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:5]([CH3:12])=[C:6]([OH:11])[CH:7]=[CH:8][C:9]=1[Cl:10].I[CH3:14].O>CN(C=O)C>[Cl:10][C:9]1[C:4]([NH2:3])=[C:5]([CH3:12])[C:6]([O:11][CH3:14])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 227088313-Amino-4-chloro-2-methylphenol

Product 1

HCID 22708811HCID 22708811, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH, 60% (0.236 mol) was stirred in DMF (500 ml), at room temperature. 3-amino-4-chloro-2-methylphenol (0.236 mol) was added portionwise (exothermic temperature rise to 32° C.). The reaction mixture was stirred for 30 minutes, allowing the temperature to drop to room temperature. Iodomethane (0.236 mol) was added dropwise. The reaction mixture was stirred for one hour at room temperature. Water was added (at first, slowly). This mixture was extracted with toluene. The separated organic layer was dried, filtered and the solvent evaporated, yielding 40.5 g 6-chloro-3-methoxy-2-methylbenzenamine (interm. 22) (quantitative yield; used in next reaction step, without further purification).

Workup

  1. customto drop to room temperature
  2. stirringThe reaction mixture was stirred for one hour at room temperature
  3. extractionThis mixture was extracted with toluene
  4. customThe separated organic layer was dried
  5. filtrationfiltered
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-b57cca797832461fb35445d8f1b4f652
Source dataset
uspto-grants-2004_06
Patent number
US06750349B2

Reaction notes

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