Acetic Anhydride → HCID 57845548, compound
Reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.C([O-])(=O)C.[Na+].[NH2:13][CH2:14][C:15]([C:17]1[CH:18]=[N:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=1)=[O:16]>O>[N+:23]([C:20]1[N:19]=[CH:18][C:17]([C:15](=[O:16])[CH2:14][NH:13][C:5](=[O:7])[CH3:6])=[CH:22][CH:21]=1)([O-:25])=[O:24]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
1.575 cm3 (16.66 mmol) of acetic anhydride and then 1.367 g (16.66 mmol) of sodium acetate in solution in 3 cm3 of water are added at a temperature in the region of 5° C. to 1.05 g (4.166 mmol) of 2-amino-1-(6-nitropyridin-3-yl)-ethanone in solution in 25 cm3 of water. After stirring for 3 hours at 5° C., the reaction mixture is extracted with three times 10 cm3 of ethyl acetate. All the organic phases are combined, washed with 30 cm3 of a saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give 0.618 g of N-[2-(6-nitropyridin-3-yl)-2-oxoethyl]acetamide, in the form of a yellow solid. 1H NMR (400 MHz, (CD3)2SO, —δ in ppm) 1.90 (s, 3H); 4.66 (d, J=4.5 Hz, 2H); 8.37 (broad t, J=4.5 Hz, 1H); 8.43 (d, J=8.5 Hz, 1H); 8.68 (dd, J=2.0 and 8.5 Hz, 1H); 9.16 (d, J=2.0 Hz, 1H). 2-Amino-1-(6-nitropyridin-3-yl)ethanone may be prepared in the following manner:
Workup
- extractionthe reaction mixture is extracted with three times 10 cm3 of ethyl acetate
- washwashed with 30 cm3 of a saturated aqueous sodium chloride solution
- dry with materialdried over anhydrous magnesium sulphate
- filtrationfiltered
- concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
Sources & evidence
- ORD record
- ord-5c2bf48b302f4c098de68d47c253bfaf
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07592365B2
Reaction notes
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