Benzylamine → HCID 22034114, compound

HRID 639618Notes

Reaction equation

HRID 639618 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[CH:5]=[C:4]([CH3:12])[N:3]=1.C(N(CC)CC)C.[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[CH2:20]([NH:27][C:6]1[CH:5]=[C:4]([CH3:12])[N:3]=[C:2]([Cl:1])[C:7]=1[N+:8]([O-:10])=[O:9])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 27848192,4-Dichloro-6-methyl-3-nitropyridine

Product 1

HCID 22034114HCID 22034114, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2,4-Dichloro-6-methyl-3-nitro-pyridine (2 g, 9.7 mmol) and triethylamine (1.35 mL, 9.7 mmol) were dissolved in 40 mL THF and cooled (ice/water) to ˜5° C. A solution of benzylamine (1.04 g, 9.7 mmol) in 10 mL THF was added dropwise and the mixture was then allowed to warm gradually to room temperature overnight. The mixture was evaporated in vacuo, partitioned between EtOAc (50 mL) and water (20 mL). The organic layer was washed with saturated aqueous NaHCO3 (10 mL), dried (MgSO4) and evaporated in vacuo to an orange gum. This gum was preabsorbed onto silica gel and then purified by column chromatography, eluting with DCM:pentane 3:1. Appropriate fractions combined and evaporated in vacuo to yield the title compound as a yellow solid (716 mg).

Workup

  1. customThe mixture was evaporated in vacuo
  2. custompartitioned between EtOAc (50 mL) and water (20 mL)
  3. washThe organic layer was washed with saturated aqueous NaHCO3 (10 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo to an orange gum
  6. customThis gum was preabsorbed onto silica gel
  7. custompurified by column chromatography
  8. washeluting with DCM:pentane 3:1
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-0fcd44aaa5164f4ba1e29242d217f18b
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

Loading…