Benzylamine → HCID 76851416, compound

HRID 639695Notes

Reaction equation

HRID 639695 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[C:5]([CH3:12])=[C:4]([CH3:13])[N:3]=1.[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CCOC(C)=O>[CH2:14]([NH:21][C:6]1[C:5]([CH3:12])=[C:4]([CH3:13])[N:3]=[C:2]([Cl:1])[C:7]=1[N+:8]([O-:10])=[O:9])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 121091232,4-Dichloro-5,6-dimethyl-3-nitropyridine

Product 1

HCID 76851416HCID 76851416, compoundYield 45.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

2,4-Dichloro-5,6-Dimethyl-3-nitro-pyridine (2 g, 9 mmol) was dissolved in acetonitrile (100 mL) and benzylamine (1.0 mL, 9.5 mmol). Potassium carbonate (1.3 g, 9.5 mmol) was added in one portion, and the whole was heated at 55° C. for 16 h. The reaction mixture was diluted with EtOAc and washed with 50 mL water. The aqueous was re-extracted with EtOAc, the organics were combined and then dried over MgSO4 and evaporated to a dark red residue. This residue was purified by column chromatography on silica gel using 8:1 pentane:EtOAc as eluant to afford the title compound as a bright orange solid (1.2 g, 45%).

Workup

  1. washwashed with 50 mL water
  2. extractionThe aqueous was re-extracted with EtOAc
  3. dry with materialdried over MgSO4
  4. customevaporated to a dark red residue
  5. customThis residue was purified by column chromatography on silica gel using 8:1 pentane

Sources & evidence

ORD record
ord-1de921a7f5824d188d0ffceaf35c946b
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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