Hydrochloric Acid → HCID 86746762, compound
Reaction equation
[C:1]([C:8]1C=CC(C(O)=O)=[C:10]([NH:17]N)[CH:9]=1)([O:3]C(C)(C)C)=O.[NH:19]([C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)[NH2:20].C(N(CC)CC)C.CC([O:41]C(ON=C(C1C=CC=CC=1)C#N)=O)(C)C.[ClH:55]>CN(C)C=O>[ClH:55].[ClH:55].[NH:19]([C:21]1[CH:22]=[CH:23][C:24]([C:25]([O:27][N:17]2[C:1](=[O:3])[CH2:8][CH2:9][C:10]2=[O:41])=[O:26])=[CH:28][CH:29]=1)[NH2:20]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
Synthesis of 4-BOC-hydrazinobenzoic acid--To a stirred solution of 4-hydrazinobenzoic acid (1 equivalent) and triethylamine (3 equivalents) in dimethylformamide (5 mg/1) was added dropwise a solution of BOC-ON (1 equivalent) in dimethylformamide. The reaction mixture was stirred at room temperature for 3 hours. Ten percent aqueous hydrochloric acid was added and subsequently the solution became cloudy. The solution was extracted with ethyl acetate and the combined organic extracts were washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give a brown solid. The solid was recrystallized from chloroform to give the desired product as a pale brown solid; yield 69%. Analysis:
Workup
- extractionThe solution was extracted with ethyl acetate
- washthe combined organic extracts were washed with water
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customto give a brown solid
- customThe solid was recrystallized from chloroform
Sources & evidence
- ORD record
- ord-a31c8f5e691c44ef907ba1b6dd7cc720
- Source dataset
- uspto-grants-1993_04
- Patent number
- US05206370
Reaction notes
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