US 7,531,691 B2
Method for producing naphthalene carboxylic acid amide compound
Hiroyuki Wakamori, Osaka (Japan); and Nobuhiro Yonetani, Osaka (Japan)
Assigned to Ueno Fine Chemicals Industry, Ltd., Osaka-fu (Japan)
Filed on Jun. 11, 2007, as Appl. No. 11/808,503.
Claims priority of application No. 2006-167463 (JP), filed on Jun. 16, 2006.
Prior Publication US 2008/0045720 A1, Feb. 21, 2008
Int. Cl. C07C 231/00 (2006.01)
U.S. Cl. 564—142 8 Claims
 
1. A method for producing a naphthalenecarboxylic acid amide compound represented by formula [1] comprising, reacting a naphthalenecarboxylic acid halide compound represented by formula [2] with ammonium acetate in a solvent having an ether bond:

OG Complex Work Unit Drawing
wherein, Hal is chlorine or bromine;
m is an integer of 1 or 2;
R is selected from the group consisting of hydrogen, an optionally branched saturated alkyl having 1-20 carbon atoms, an aralkyl having 7-12 carbon atoms, an optionally branched saturated alkanoyl having 2-20 carbon atoms and benzoyl group;
X is selected from the group consisting of hydrogen, cyano, a group represented by formulae [3], [4] and [5]:

OG Complex Work Unit Drawing
provided that when m is 2, X is hydrogen;
n is an integer of 1 or 2;
Y1 is selected from the group consisting of hydrogen, an optionally branched and optionally unsaturated aliphatic group having 1-20 carbon atoms, an optionally substituted aromatic group and an optionally substituted heterocyclic group having conjugated double bonds;
Y2 is an optionally branched and optionally unsaturated aliphatic group having 1-20 carbon atoms;
Z is —O—, —S— or —NH—; and
A is selected from the group consisting of an optionally substituted aromatic group and an optionally substituted heterocyclic group having conjugated double bonds.