Hydroxylamine → 2,5-dichloro-N-hydroxy-4,6-dimethylpyridine-3-carboximidamide

HRID 2274735Notes

Reaction equation

HRID 2274735 reaction equation
[Cl:1][C:2]1[N:9]=[C:8]([CH3:10])[C:7]([Cl:11])=[C:6]([CH3:12])[C:3]=1[C:4]#[N:5].[NH2:13][OH:14].O.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.O>CO.O>[Cl:1][C:2]1[N:9]=[C:8]([CH3:10])[C:7]([Cl:11])=[C:6]([CH3:12])[C:3]=1/[C:4](=[N:13]/[OH:14])/[NH2:5]

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 962WaterHCID 212261,10-Phenanthroline hydrateHCID 3348522,5-Dichloro-4,6-dimethylnicotinonitrile

Product 1

HCID 462051712,5-dichloro-N-hydroxy-4,6-dimethylpyridine-3-carboximidamide

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
75 °C

Procedure

A suspension of 2,5-Dichloro-4,6-dimethyl-nicotinonitrile (45.0 kg) and 50% hydroxylamine (59.2 kg) in the presence of catalytic amount of 1,10-phenanthroline monohydrate (0.680 kg) in methanol/water (214 kg/362 kg) is heated to 70-80° C. The mixture is agitated at 70-80° C. Water (353 kg) is added slowly into the resulting solution while the temperature is maintained at >79° C. The solution is cooled to 75° C. with stirring resulting in crystallization of (Z)-2,5-dichloro-N′-hydroxy-4,6-dimethylnicotinimidamide. The suspension is further cooled to 20° C., the solid is filtered off and the wet cake is washed with water (160 kg). (Z)-2,5-dichloro-N′-hydroxy-4,6-dimethylnicotinimidamide is dried under vacuum at max. 60° C. until residual water level is max 0.15% (KF).

Workup

  1. temperatureis maintained at >79° C
  2. temperatureThe solution is cooled to 75° C.
  3. stirringwith stirring

Sources & evidence

ORD record
ord-1ed0d7dd83264926b7db9c744945c45b
Source dataset
uspto-grants-2015_09
Patent number
US09126988B2

Reaction notes

Loading…