Benzylamine → HCID 86614467, compound

HRID 639615Notes

Reaction equation

HRID 639615 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([Cl:10])[C:7]([N+:11]([O-:13])=[O:12])=[C:6](Cl)[CH:5]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[CH2:22]([NH:29][C:6]1[CH:5]=[C:4]([CH:1]2[CH2:3][CH2:2]2)[N:9]=[C:8]([Cl:10])[C:7]=1[N+:11]([O-:13])=[O:12])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 86614468HCID 86614468, compound

Product 1

HCID 86614467HCID 86614467, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Cyclopropyl-2,4-dichloro-3-nitro-pyridine (160 mg, 0.8 mmol) was dissolved in THF (2 mL) and triethylamine (104□l, 0.8 mmol) and benzylamine (81□l, 0.8 mmol) were added. The mixture was stirred at room temperature under a nitrogen atmosphere for 48 hours by which time a yellow precipitate had formed. The volatiles were removed in vacuo and the residue was stored in a stoppered flask at room temperature for 10 days. The residue was purified by column chromatography on silica gel eluting with 99:1 DCM:MeOH then 98:2 DCM:MeOH to give the title compound (185 mg) as a yellow crystalline solid.

Workup

  1. customhad formed
  2. customThe volatiles were removed in vacuo
  3. waitthe residue was stored in a stoppered flask at room temperature for 10 days
  4. customThe residue was purified by column chromatography on silica gel eluting with 99:1 DCM

Sources & evidence

ORD record
ord-24da386ef62047c9bb6152558491e25c
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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