Sodium Carbonate → 1,2,3,9-Tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one

HRID 2309419Notes

Reaction equation

HRID 2309419 reaction equation
[I-].C[N+](C)(C)[CH2:4][CH:5]1[C:17](=[O:18])[C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([CH3:19])[C:8]=2[CH2:7][CH2:6]1.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:19][N:9]1[C:8]2[CH2:7][CH2:6][C:5](=[CH2:4])[C:17](=[O:18])[C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 135197122,3,4,9-Tetrahydro-N,N,N,9-tetramethyl-4-oxo-1H-carbazole-3-methanaminium iodide

Product 1

HCID 117905051,2,3,9-Tetrahydro-9-methyl-3-methylene-4H-carbazol-4-oneYield 105.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the product from Preparation 2 (5.0 g) in water (20 ml) was treated with 2N sodium carbonate (6.55 ml) and warmed at 35° for 45 mins. The resulting slurry was cooled to 0° and the solid was filtered off, washed with water and dried to give the title compound (2.8 g) m.p. 127°-129°.

Workup

  1. temperaturewarmed at 35° for 45 mins
  2. temperatureThe resulting slurry was cooled to 0°
  3. filtrationthe solid was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-fc03eb48440743b3be6ecee9a616edb7
Source dataset
uspto-grants-1987_09
Patent number
US04695578

Reaction notes

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