N-methyl-2-pyrrolidone → 3-Cyano-5-[(dipropylamino)carbonyl]Benzoic Acid
Reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([N:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:20][N:21]1CCCC1=O>>[C:20]([C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([N:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6])#[N:21]Participants
Conditions
- Temperature
- 175 °C
Procedure
A mixture of 3-bromo-5-[(dipropylamino)carbonyl]benzoic acid (PREPARATION 4, 0.596 g, 1.82 mmol) and copper nitrile (0.325 g, 3.63 mmol) in N-methylpyrrolidinone (1.5 mL) is stirred at 175 degrees C. for 2.5 hour, at which time the mixture is cooled and partitioned between ethyl acetate and hydrochloric acid (3N). The organic layer is washed twice more with hydrochloric acid (3N) and then twice more with saline which had been acidified with a small amount of hydrochloric acid (3N). The organic layer is dried over magnesium sulfate and concentrated under high vacuum to give the title compound, NMR (CDCl3) delta 0.80, 1.02, 1.60, 1.73, 3.17, 3.51, 7.90, 8.31 and 8.41; an aliquot is crystallized from ethyl ether/dichloromethane/hexane—IR (diffuse reflectance) 3017, 2970, 2937, 2898, 2877, 2473, 2432, 2350, 2318, 2236, 1721, 1608, 1588, 1206 and 1196 cm−1.
Workup
- temperatureat which time the mixture is cooled
- custompartitioned between ethyl acetate and hydrochloric acid (3N)
- washThe organic layer is washed twice more with hydrochloric acid (3N)
- dry with materialThe organic layer is dried over magnesium sulfate
- concentrationconcentrated under high vacuum
Sources & evidence
- ORD record
- ord-8bcb4de8ccbc4622a194a62f4ea5c5f4
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07553831B2
Reaction notes
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