Hydroxylamine → 6-Fluoro-1H-indole-3-carbonitrile

HRID 1258179Notes

Reaction equation

HRID 1258179 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=O)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[NH2:13]O.C([O-])=O.[Na+].O>C(O)=O>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]#[N:13])=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 962WaterHCID 2629036-Fluoroindole-3-carboxaldehydeHCID 2723810Sodium Formate

Product 1

HCID 534187306-Fluoro-1H-indole-3-carbonitrileYield 59.9%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-fluoro-1H-indole-3-carbaldehyde (0.97 g) in 90% formic acid (25 mL) were added hydroxylamine (0.65 g) and sodium formate (0.81 g), and this mixture was stirred at 100° C. for 3 hours. After cooling to ambient temperature, water was added to this reaction mixture and the precipitated solid was collected by filtration, and washed with water, dried to give the title compound (0.57 g).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-e6d7f7ddc5434999990874f659f7d332
Source dataset
uspto-grants-2013_06
Patent number
US08466152B2

Reaction notes

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