Dimethylformamide → HCID 14233935, compound

HRID 1723281Notes

Reaction equation

HRID 1723281 reaction equation
[F:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[C:7](=[O:15])[CH2:8][CH2:9][CH2:10][C:11]=3[NH:12]2)=[CH:4][CH:3]=1.[CH3:16]N(C=O)C>>[F:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[C:7](=[O:15])[CH2:8][CH2:9][CH2:10][C:11]=3[N:12]2[CH3:16])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 14233934HCID 14233934, compound

Product 1

HCID 14233935HCID 14233935, compound

Procedure

A solution of 7-fluoro-1,2,3,9-tetrahydro-4H-carbazol-4-one (1.0 g) in dry DMF (8 ml) was added dropwise to a stirred, ice-cooled suspension of pre-washed (hexane:2×10 ml) sodium hydride (78% dispersion in oil; 175 mg) in dry DMF (5 ml) under nitrogen and stirring was continued at room temperature for 1.5 h. The solution was cooled to 0°, iodomethane (0.35 ml) was added dropwise and stirring was continued at 0° for 2 h. The suspension was poured into 8% aqueous sodium bicarbonate (30 ml) extracted with dichloromethane (2×30 ml) and the combined, dried organic extracts were evaporated and dried in vacuo at 100° for 18 h to give the title compound (1.03 g) as a solid, m.p. 174°-175°.

Workup

  1. temperaturecooled
  2. additionsuspension
  3. washof pre-washed (hexane:2×10 ml) sodium hydride (78% dispersion in oil; 175 mg) in dry DMF (5 ml) under nitrogen
  4. temperatureThe solution was cooled to 0°
  5. additioniodomethane (0.35 ml) was added dropwise
  6. stirringstirring
  7. waitwas continued at 0° for 2 h
  8. additionThe suspension was poured into 8% aqueous sodium bicarbonate (30 ml)
  9. extractionextracted with dichloromethane (2×30 ml)
  10. customdried organic extracts were evaporated
  11. customdried in vacuo at 100° for 18 h

Sources & evidence

ORD record
ord-1f16384b47ae404fb00536289bed0f74
Source dataset
uspto-grants-1989_08
Patent number
US04859662

Reaction notes

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