Hydroxyamine hydrochloride → HCID 73654202, compound

HRID 2081206Notes

Reaction equation

HRID 2081206 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](=O)[C:7]2=1.Cl.[NH2:18][OH:19]>N1C=CC=CC=1>[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:18][OH:19])[C:7]2=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 197698468-Fluoro-9-methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one

Product 1

HCID 73654202HCID 73654202, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 8-fluoro-1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one (3.0 g) and hydroxylamine hydrochloride (2.92 g) in pyridine (ca. 35 ml) was heated at 60° for 3 h. The solution was concentrated in vacuo then azeotropically dried with toluene (2×10 ml). The residue was treated with 8% sodium bicarbonate solution (125 ml) and extracted with ethyl acetate (3×100 ml). The combined extracts were filtered and concentrated in vacuo to give the title compound (1.8 g) as a solid, t.l.c. (System A, 100:8:1) Rf 0.66.

Workup

  1. temperaturewas heated at 60° for 3 h
  2. concentrationThe solution was concentrated in vacuo
  3. dry with materialthen azeotropically dried with toluene (2×10 ml)
  4. additionThe residue was treated with 8% sodium bicarbonate solution (125 ml)
  5. extractionextracted with ethyl acetate (3×100 ml)
  6. filtrationThe combined extracts were filtered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-17fb70c0ec7743a3875a61c35adcfdf8
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

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