Glycine → Acetic acid, 2-((2-chlorobenzoyl)amino)-
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:11][CH2:12][C:13]([OH:15])=[O:14]>>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:11][CH2:12][C:13]([OH:15])=[O:14])=[O:5]Participants
3
Procedure
Commercially available 2-chlorobenzoyl chloride was treated with glycine to give 2-(2-chlorobenzamido)acetic acid 21 in good yield. Then, 21 was reacted with acetic anhydride and benzaldehyde, in the presence of sodium acetate, to lead to the corresponding oxazolone in excellent yield. The resulting (4Z)-4-benzylidene-2-(2-chlorophenyl)oxazol-5(4H)-one 22 was converted via a Friedel-Crafts reaction to 1-(2-chlorophenyl)isoquinoline-3-carboxylic acid 23 in moderate yield2. Finally, the dimeric compounds 24 were easily obtained in good yields by transformation of the acid into acylchloride and further reactions with diamines.
Sources & evidence
- ORD record
- ord-0265f1affbb64facaf2cf661fd11d395
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541428B2
Reaction notes
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