Methyl iodide → 8-Fluoro-9-methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one

HRID 2081203Notes

Reaction equation

HRID 2081203 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:16]=1[NH:15][C:14]1[CH2:13][CH2:12][CH2:11][C:10](=[O:17])[C:9]2=1.[CH3:18]I>C1COCC1.[Cl-].[Na+].O>[F:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:16]=1[N:15]([CH3:18])[C:14]1[CH2:13][CH2:12][CH2:11][C:10](=[O:17])[C:9]2=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 221477458-Fluoro-1,2,3,9-tetrahydro-4H-carbazol-4-one

Product 1

HCID 197698468-Fluoro-9-methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a suspension of sodium hydride (80% dispersion in oil; 1.15 g) in dry THF (50 ml) under nitrogen was added 8-fluoro-1,2,3,9-tetrahydro-4H-carbazol-4-one (6.5 g) in dry THF (50 ml), and the mixture was stirred for 1 h. Methyl iodide (4.1 ml) was added, and the mixture was stirred for 3 h. The mixture was then poured into brine (300 ml) and extracted with ether (2×300 ml). The combined, dried organic extracts were evaporated in vacuo to give the title compound (5.77 g), m.p. 126°-128°.

Workup

  1. stirringthe mixture was stirred for 3 h
  2. extractionextracted with ether (2×300 ml)
  3. customdried organic extracts were evaporated in vacuo

Sources & evidence

ORD record
ord-1acd791192e44d3ca0311460bd800942
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

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