Water → HCID 15712516, compound

HRID 2081207Notes

Reaction equation

HRID 2081207 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:14]=1[N:13]([CH3:15])[C:12]1[CH2:11][CH2:10][CH2:9][C:8](=[N:16]O)[C:7]2=1.[OH2:18]>O1CCOCC1.CO>[F:1][C:2]1[C:14]2[N:13]([CH3:15])[C:12]3[CH2:11][CH2:10][CH2:9][NH:16][C:8](=[O:18])[C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 962WaterHCID 73654202HCID 73654202, compound

Product 1

HCID 15712516HCID 15712516, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 8-fluoro-1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one oxime (1.8 g) and polyphosphoric acid (ca. 20 ml) in dioxan (30 ml) was stirred under nitrogen at 100°-110° for 1 h. After cooling, the reaction mixture was poured into iced water (1 l) and the resulting suspension was extracted with dichloromethane. The organic extract was concentrated in vacuo to give a solid which was taken up in methanol and adsorbed onto silica. Purification by FCC eluting with System A (200:8:1) gave the title compound (850 mg), m.p. 233°-235°.

Workup

  1. temperatureAfter cooling
  2. extractionthe resulting suspension was extracted with dichloromethane
  3. extractionThe organic extract
  4. concentrationwas concentrated in vacuo
  5. customto give a solid which
  6. customPurification by FCC
  7. washeluting with System A (200:8:1)

Sources & evidence

ORD record
ord-96f04fabce564f15901f710ff82c279f
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

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