Hydrochloric Acid → 2-Chloro-5-(2,4-dichloro-phenyl)-isonicotinonitrile

HRID 420499Notes

Reaction equation

HRID 420499 reaction equation
N[C:2]1[CH:3]=[C:4]([C:7]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])=[CH:8][N:9]=1)[C:5]#[N:6].N([O-])=O.[Na+].[ClH:22]>>[Cl:22][C:2]1[CH:3]=[C:4]([C:7]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])=[CH:8][N:9]=1)[C:5]#[N:6]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 451233422-Amino-5-(2,4-dichlorophenyl)isonicotinonitrile

Product 1

HCID 451233412-Chloro-5-(2,4-dichloro-phenyl)-isonicotinonitrileYield 48%

Procedure

A mixture of 2-amino-5-(2,4-dichloro-phenyl)-isonicotinonitrile (880 mg, 3.3 mmol) in HCl conc. (15 mL) was vigorously stirred and cooled to −15° C. (ice/MeOH bath). NaNO2 (4.6 g, 66.7 mmol) was carefully added, then the reaction mixture was slowly warmed to RT and stirred for 24 h. The formed precipitate was filtered, washed with water, and purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→5:95) to yield the title compound (453 mg, 1.6 mmol, 48%). MS: 284 [M+1]+; HPLC: AtRet=2.70.

Workup

  1. stirringstirred for 24 h
  2. filtrationThe formed precipitate was filtered
  3. washwashed with water
  4. custompurified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→5:95)

Sources & evidence

ORD record
ord-9b0be04c79b44204a9ffab1179f8eaba
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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