Potassium Carbonate → HCID 43330318, compound

HRID 1749072Notes

Reaction equation

HRID 1749072 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.Cl[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[C:13]([Cl:20])[N:12]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:11]2[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[C:13]([Cl:20])[N:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 660364-ChlorobenzylamineHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 43330318HCID 43330318, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Chlorobenzylamine (7.3 mL, 60 mmol) was added dropwise to a stirred, cooled (˜0° C.), solution of 2,6-dichloro-3-nitropyridine (10.1 g, 52.2 mmol) and K2CO3 (7.93 g, 57.4 mmol) in MeCN (60 mL). After stirring for 5 hours at ambient temperature, the mixture was concentrated in vacuo and then partitioned between EtOAc and water. The EtOAc layer was then washed successively with aqueous potassium hydrogen sulfate solution, brine and then dried (MgSO4). The solution was evaporated in vacuo to give a yellow solid which was recrystallised from heptane/EtOAc (1:2) to give (4-chloro-benzyl)-(6-chloro-3-nitro-pyridin-2-yl)-amine as a yellow solid (7.67 g). The mother liquor was evaporated and the residue recrystallised from EtOH to give a second crop of product (3.39 g). MS: [M+H]+=298

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. custompartitioned between EtOAc and water
  3. washThe EtOAc layer was then washed successively with aqueous potassium hydrogen sulfate solution, brine
  4. dry with materialdried (MgSO4)
  5. customThe solution was evaporated in vacuo
  6. customto give a yellow solid which
  7. customwas recrystallised from heptane/EtOAc (1:2)

Sources & evidence

ORD record
ord-4f3584ec9d924aa49a627f308e4a6e1d
Source dataset
uspto-grants-2015_10
Patent number
US09155743B2

Reaction notes

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