Sodium Hydroxide → 1-(4-nitrophenyl)-5-propyl-1H-1,2,3-triazole-4-carboxylic acid
Reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].O=[C:14]([CH2:21][CH2:22][CH3:23])[CH2:15][C:16]([O:18]CC)=[O:17].C[O-].[Na+].[OH-].[Na+]>CO>[N+:10]([C:7]1[CH:8]=[CH:9][C:4]([N:1]2[C:14]([CH2:21][CH2:22][CH3:23])=[C:15]([C:16]([OH:18])=[O:17])[N:3]=[N:2]2)=[CH:5][CH:6]=1)([O-:12])=[O:11]Participants
Procedure
To a solution of 1-azido-4-nitrobenzene (16.4 g) obtained in Example 1a) and ethyl 3-keto-n-hexanoate (17.0 ml) in methanol (200 ml) was added 28% sodium methoxide in methanol solution (21 ml) under ice-cooling, and the mixture was stirred for 30 min and then at 50° C. overnight. Then, 1N aqueous sodium hydroxide solution (100 ml) was added, and the mixture was stirred at 50° C. for 1.5 hr, and cooled to room temperature. The solvent was evaporated under reduced pressure, and the residual aqueous solution was diluted with water and washed with ethyl acetate. Then, the mixture was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound as a brown solid (13.4 g, 49%). The obtained crude product was used for the next reaction without further purification.
Workup
- temperaturecooling
- customat 50° C.
- customovernight
- stirringthe mixture was stirred at 50° C. for 1.5 hr
- customThe solvent was evaporated under reduced pressure
- additionthe residual aqueous solution was diluted with water
- washwashed with ethyl acetate
- extractionextracted with ethyl acetate
- dry with materialThe extract was dried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-b81f4b26242d45c5ad5b7f0fc3cc51c4
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07803822B2
Reaction notes
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