Acetic Anhydride → 2-Chloro-3-(2-nitroethenyl)pyridine

HRID 84959

Reaction equation

HRID 84959 reaction equation
Cl[C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[ClH:10].[CH2:11]([NH2:13])C.[OH-:14].[Na+].C(N(CC)CC)C.C(OC(=O)C)(=[O:25])C.C([O-])(O)=O.[Na+]>[N+](C)([O-])=O.C(O)C.CN(C)C1C=CN=CC=1>[Cl:10][C:2]1[C:3](/[CH:4]=[CH:11]/[N+:13]([O-:25])=[O:14])=[CH:6][CH:7]=[CH:8][N:9]=1

Participants

10

Reactant 6

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 11198Ethylamine hydrochlorideHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 7376072-Chloro-3-pyridinecarboxaldehyde

Product 1

HCID 866478022-Chloro-3-(2-nitroethenyl)pyridine

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 702EthanolSolventHCID 6375NitromethaneSolvent

Procedure

To 2-chloronicotinaldehyde (2.8 g, 19.8 mmol) in nitromethane (6.1 g) was added ethylamine hydrochloride (100 mg, 1.2 mmol) and NaOH (25 mg) in ethanol (1.5 mL). The mixture was stirred for 1 hour and concentrated. The crude was dissolved in CH2Cl2 (30 mL) and treated with triethylamine (2.8 g, 28 mmol), 4-(dimethylamino)pyridine (20 mg) and acetic anhydride (2.0 g, 20 mmol) at 0° C. The mixture was stirred for 15 minutes and concentrated saturated NaHCO3(aq) was added, and the precipitates were collected to afford the title compound.

Workup

  1. concentrationconcentrated
  2. dissolutionThe crude was dissolved in CH2Cl2 (30 mL)
  3. stirringThe mixture was stirred for 15 minutes
  4. customthe precipitates were collected

Sources & evidence

ORD record
ord-0d7f2a7594ea4a23a28dd954e555d644
Source dataset
uspto-grants-2014_09
Patent number
US08846951B2

Linked notes

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