Dimethylformamide → Morpholine
Reaction equation
[N+]([C:4]1C=[C:6]2[CH:12]=[C:11]([C:13]([OH:15])=O)[NH:10][C:7]2=[N:8][CH:9]=1)([O-])=O.[CH3:16][N:17]([CH3:20])[CH:18]=O>>[NH:10]1[CH2:7][CH2:6][O:15][CH2:13][CH2:11]1.[CH3:16][N:17]([CH3:20])[CH2:18][CH2:4][CH2:9][N:8]=[C:7]=[N:10][CH2:11][CH3:12]Participants
4
Procedure
A flask is charged successively with 600 mg (2.90 mmol) of the 5-nitro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid formed during the preceding stage, 10 mL of dimethylformamide (distilled on calcium hydride), 0.5 mL (5.80 mmol) of morpholine and 1.11 g (5.80 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (EDCl) hydrochloride under argon atmosphere. The solution is stirred at room temperature for 18 hours. The solvent is then evaporated under reduced pressure and the raw product is purified directly by silica gel chromatography (ethyl acetate/methanol eluent). 313 mg of a white solid is recovered (39%).
Sources & evidence
- ORD record
- ord-51c2e2c994ec484d8839eb009b062445
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08580815B2
Reaction notes
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