Acetic Anhydride → HCID 20559958, compound
Reaction equation
C(O[C:5](=[O:7])C)(=O)C.[NH2:8][C:9]1[CH:22]=[CH:21][CH:20]=[CH:19][C:10]=1[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1>C(O)=O>[CH:5]([NH:8][C:9]1[CH:22]=[CH:21][CH:20]=[CH:19][C:10]=1[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)=[O:7]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
An aceticformic anhydride mixture is prepared by mixing acetic anhydride (140 ml.) and formic acid (70 ml.). To this mixture, 2-(o-aminophenethyl)pyridine (59 g., 0.3 mole) is added in one portion with vigorous stirring at 25° C. After 15 minutes the solution is diluted with 450 ml. of water and concentrated in vacuo. The resulting residue is taken up in 1 liter of water and made basic with 50% sodium hydroxide. The basified solution is extracted with chloroform, the chloroform extract washed with water, dried over magnesium sulfate and the chloroform solvent evaporated. Crystallization of the residue from isopropyl acetate provides 57 g. (83% yield) of 2-(o-formamidophenethyl)pyridine melting at 78°-81° C. (uncorrected). An analytical sample (from isopropyl acetate) has a melting point of 83°-83.5° C. (corr.).
Workup
- additionAfter 15 minutes the solution is diluted with 450 ml
- concentrationof water and concentrated in vacuo
- extractionThe basified solution is extracted with chloroform
- extractionthe chloroform extract
- washwashed with water
- dry with materialdried over magnesium sulfate
- customthe chloroform solvent evaporated
- customCrystallization of the residue from isopropyl acetate
- customprovides 57 g
Sources & evidence
- ORD record
- ord-ad7c55baa0304548925e37e13270a7c3
- Source dataset
- uspto-grants-1981_12
- Patent number
- USRE030812
Reaction notes
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