Ethylamine → 1-(2-Ethylamino-4-pyridyl)-1-ethanone
Reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH:8]2[O:13]CCO[CH2:9]2)[CH:5]=[CH:4][N:3]=1.[CH2:14]([NH2:16])[CH3:15]>CN1CCCC1=O>[CH2:14]([NH:16][C:2]1[CH:7]=[C:6]([C:8](=[O:13])[CH3:9])[CH:5]=[CH:4][N:3]=1)[CH3:15]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 165 °C
Procedure
A mixture of 18.8 g. (94 mmoles) of 1-(2-chloro-4-pyridyl)-1-ethylenedioxyethane and 50 ml. of ethylamine in 80 ml. of N-methyl-2-pyrrolidinone was sealed in a steel bomb and heated at 165° C. for 15 hours. The bomb was cooled and the contents distilled under reduced pressure to remove excess solvent. The residue in 100 ml. of methylene chloride was extracted with 2 N hydrochloric acid (3×25 ml.). The combined acid extracts were heated at 80° C. for 3 hours and were then cooled and made basic with sodium carbonate. The basified mixture was extracted with methylene chloride (4×25 ml.), and the combined organic extracts dried over sodium sulfate and evaporated to an oil which solidified, 11.5 g. (75%), m.p. 55°-57° C. The analytical sample was recrystallized from cyclohexane, m.p. 62°-63° C.
Workup
- additionA mixture of 18.8 g
- temperatureThe bomb was cooled
- distillationthe contents distilled under reduced pressure
- customto remove excess solvent
- extractionof methylene chloride was extracted with 2 N hydrochloric acid (3×25 ml.)
- temperatureThe combined acid extracts were heated at 80° C. for 3 hours
- temperaturewere then cooled
- extractionThe basified mixture was extracted with methylene chloride (4×25 ml.)
- dry with materialthe combined organic extracts dried over sodium sulfate
- customevaporated to an oil which
- customThe analytical sample was recrystallized from cyclohexane, m.p. 62°-63° C.
Sources & evidence
- ORD record
- ord-72cee7939b62452fa43008d1c1bc7bc0
- Source dataset
- uspto-grants-1981_11
- Patent number
- US04302464
Reaction notes
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