Water → HCID 18426777, compound

HRID 1281103Notes

Reaction equation

HRID 1281103 reaction equation
[H-].[Na+].N[C:4]1[C:5]([CH3:12])=[C:6]([OH:11])[CH:7]=[CH:8][C:9]=1[Cl:10].I[CH3:14].O.[CH3:16][N:17](C=O)C>>[Cl:10][C:9]1[C:4]([CH2:16][NH2:17])=[C:5]([CH3:12])[C:6]([O:11][CH3:14])=[CH:7][CH:8]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 227088313-Amino-4-chloro-2-methylphenol

Product 1

HCID 18426777HCID 18426777, compound

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-methylbenzylamine (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-1f67d558381b40358bfaba79e80440c7
Source dataset
uspto-grants-2002_09
Patent number
US06452013B1

Reaction notes

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