Reaction equation
N(CCC1C=CC(C(O)=O)=CC=1)C(C)=O.N(CC[C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][C:23]=1[N+:31]([O-])=O)C(C)=O>CO>[NH2:31][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:22]=1)[C:26]([OH:28])=[O:27]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
4-(2-Acetaminoethyl)-benzoic acid was reacted with nitrating acid to 4-(2-acetaminoethyl)-3-nitro-benzoic acid, M.p. 189° C. (from methanol). The following catalytical hydrogenation yielded the 4-(2-acetaminoethyl)-3-aminoethyl)-3-amino-benzoic acid with a melting point of 143° C. (from ethanol/petroleum ether). From this compound, there was obtained by diazotation and Sandmeyer-reaction the 4-(2-acetamino-ethyl)-3-chloro-benzoic acid having a melting point of 150° C. or by boiling up the diazo solution, the 4-(2-acetaminoethyl)-3-chloro-benzoic acid M.p. 222°-223° C. From 4-(2-acetaminoethyl)-3-hydroxy-benzoic acid, there were obtained with dimethyl sulfate or diethyl sulfate, the corresponding 4-(2-acetaminoethyl)-3-methoxy-benzoic acid methyl ester and the 4-(2-acetaminoethyl)-3-ethoxy-benzoic acid ethyl ester.
Sources & evidence
- ORD record
- ord-981300d1e03941baa7f21a3dc6806230
- Source dataset
- uspto-grants-1980_09
- Patent number
- US04221815
Linked notes
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