Nicotinoyl chloride → HCID 6461622, compound

HRID 450652Notes

Reaction equation

HRID 450652 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[N:8][OH:9])[NH2:7])=[CH:4][CH:3]=1.[C:12](Cl)(=O)[C:13]1[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=1>N1C=CC=CC=1>[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[N:7]=[C:12]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[O:9][N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 82604Nicotinoyl chlorideHCID 5930004-Fluoro-n-hydroxybenzimidamide

Product 1

HCID 6461622HCID 6461622, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Fluoro-N′-hydroxybenzimidamide (0.154 g, 1 mmol) was dissolved in pyridine (10 mL) and nicotinoyl chloride (Aldrich, 0.141 g, 1 mmol) was added. The reaction mixture was heated to reflux for 3 hours and then cooled to room temperature. The cooled reaction mixture was quenched with water (25 mL) and filtered. The solid was further purified with flash column chromatography (5% methanol/dichloromethane) to give the titled product. 1H NMR (300 MHz, DMSO-d6) δ 7.47 (t, J=6.8 Hz, 2 H), 7.74-7.70 (m, 1 H), 8.20-8.15 (m, 2 H), 8.58-8.54 (m, 1 H), 8.91-8.89 (dd, J=1.7, 1.7 Hz, 1 H), 9.35 (d, J=1.4 Hz, 1 H) ppm; MS (DCI/NH3) m/z 242 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. customThe cooled reaction mixture
  4. customwas quenched with water (25 mL)
  5. filtrationfiltered
  6. customThe solid was further purified with flash column chromatography (5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-72b694308712493d9e1dea3533e60bb5
Source dataset
uspto-grants-2013_07
Patent number
US08486979B2

Reaction notes

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