Glycine → Acetic acid, 2-((2-chlorobenzoyl)amino)-

反応式

[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]

参加物

反応物 2

HCID 750Glycine

HCID 691102-Chlorobenzoyl chloride

生成物 1

HCID 177756Acetic acid, 2-((2-chlorobenzoyl)amino)-

実験手順

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.

出典と根拠

ORDレコード: ord-0265f1affbb64facaf2cf661fd11d395
出典データセット: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08541428B2

反応ノート

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