Allylamine → HCID 77230200, compound
Reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.[CH2:12]([NH2:15])[CH:13]=[CH2:14]>C(Cl)Cl>[Cl:11][C:4]1[N:3]=[C:2]([NH:15][CH2:12][CH:13]=[CH2:14])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -15 °C
Procedure
2,6-Dichloro-3-nitropyridine (71-1, 10 g, 51.8 mmol, 1.0 equiv) was added to anhydrous DCM (207 mL) and cooled to −15° C. TEA (7.57 mL, 53.9 mmol, 1.04 equiv) was then added followed by allyl amine (4.05 mL, 53.9 mmol, 1.04 equiv) over 12 h via syringe pump. Following this duration, the reaction vessel was removed from the −15° C. bath and allowed to gradually warm to RT. After 18 h, the reaction was quenched with 0.2M citric acid (100 mL) and diluted with CH2Cl2 (40 mL). The layers were separated and the organics were washed an additional time with 1×100 mL 0.2M citric acid. Washed combined organics with 2×100 mL sat. NaHCO3, dried over Na2SO4, filtered and concentrated to give an orange oil. The crude material was carried onward without further purification. LRMS (M+H)+: observed=214.0, calculated=213.6.
Workup
- customthe reaction vessel was removed from the −15° C. bath
- temperatureto gradually warm to RT
- customthe reaction was quenched with 0.2M citric acid (100 mL)
- additiondiluted with CH2Cl2 (40 mL)
- customThe layers were separated
- washthe organics were washed an additional time with 1×100 mL 0.2M citric acid
- washWashed
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customto give an orange oil
- customThe crude material was carried onward without further purification
Sources & evidence
- ORD record
- ord-d891188ad47a45418c4f38e8df49f6b6
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765784B2
Reaction notes
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