Benzene → 9-Methyl-9h-carbazol-2-ol

HRID 744874Notes

Reaction equation

HRID 744874 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]=2[CH:3]=1.[OH-].[Na+].[CH:17]1C=CC=CC=1.CI>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([CH3:17])[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 935512-Hydroxycarbazole

Product 1

HCID 1878409-Methyl-9h-carbazol-2-ol

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

To a mixture comprising 20 g of 2-hydroxycarbazole, 3 g of benzyltriethyl ammonium chloride, 70 ml of a 50% aqueous solution of sodium hydroxide and 10 ml of benzene was added dropwise 25 g of methyl iodide. After the dropwise addition, the mixture was stirred for 2 hours. The mixture was poured into hot water and the mixture was allowed to stand at room temperature overnight. The precipitated solid was recovered by filtration, washed with water and dried to obtain a yellowish brown solid of 2-hydroxy-9-methylcarbazole.

Workup

  1. additionAfter the dropwise addition
  2. waitto stand at room temperature overnight
  3. filtrationThe precipitated solid was recovered by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-975037668a094fdd82e19f58a1c40dbe
Source dataset
uspto-grants-1996_09
Patent number
US05559231

Reaction notes

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