Methyl iodide → 9-Methyl-9H-carbazole-3-carboxylic acid

HRID 566616Notes

Reaction equation

HRID 566616 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([C:14]([OH:16])=[O:15])[CH:2]=1.[C:17]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH3:17][N:12]1[C:13]2[CH:1]=[CH:2][C:3]([C:14]([OH:16])=[O:15])=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 31520239H-Carbazole-3-carboxylic acid

Product 1

HCID 6144939-Methyl-9H-carbazole-3-carboxylic acidYield 87.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 9H-carbazole-3-carboxylic acid (300 mg, 1.42 mmol), K2CO3 (800 mg) and methyl iodide (1 mL) in 25 mL of acetone was heated under reflux overnight, then cooled and evaporated in vacuo. A mixture of the resultant residue and NaOH (170 mg) in aqueous MeOH (90%, 25 mL) was stirred at 50° C. for 30 minutes. The reaction mixture was concentrated and acidified with diluted HCl. The solids were collected by filtration and dried to give the title compound (280 mg, 87%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. temperaturecooled
  4. customevaporated in vacuo
  5. additionA mixture of the resultant residue and NaOH (170 mg) in aqueous MeOH (90%, 25 mL)
  6. concentrationThe reaction mixture was concentrated
  7. filtrationThe solids were collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-d7b0670bf3d4493391d9d4d4c1c681b1
Source dataset
uspto-grants-2001_01
Patent number
US06175015B1

Reaction notes

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