US 12,122,755 B2
Methods for producing nitroso compound and quinoxaline compound
Ryuji Tamai, Tokyo (JP); Yukio Uchida, Tokyo (JP); Fumiaki Takabe, Tokyo (JP); Akira Kato, Tokyo (JP); Ryo Maruyama, Tokyo (JP); and Ryo Kobayashi, Tokyo (JP)
Assigned to Kumiai Chemical Industry Co., Ltd., Tokyo (JP)
Filed by Kumiai Chemical Industry Co., Ltd., Tokyo (JP)
Filed on Sep. 28, 2022, as Appl. No. 17/954,740.
Application 17/954,740 is a division of application No. 17/253,823, granted, now 11,492,334, previously published as PCT/JP2020/003687, filed on Jan. 31, 2020.
Claims priority of application No. 2019-014969 (JP), filed on Jan. 31, 2019.
Prior Publication US 2023/0074836 A1, Mar. 9, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 241/44 (2006.01); C07C 213/08 (2006.01)
CPC C07D 241/44 (2013.01) [C07C 213/08 (2013.01); C07C 2601/16 (2017.05)] 5 Claims
 
1. A method for producing a compound of a formula (3), comprising reacting a compound of a formula (1) with a compound of a formula (2) by using a tertiary alcohol and a base:

OG Complex Work Unit Chemistry
wherein R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each independently a hydrogen atom, a halogen atom, a (C1-C4) alkyl, or a (C1-C4) alkoxy,
wherein the amount of the base used is 2.0 equivalents to 4.0 equivalents per 1 equivalent of the compound of the formula (2), and the amount of the tertiary alcohol used is 0.3 equivalents to 2.5 equivalents per 1 equivalent of the compound of the formula (2),
wherein the base comprises a plurality of compounds comprising a lithium-containing base as a first compound, and a second compound selected from the group consisting of alkali metal hydrides and alkali metal amides,
wherein the reaction is performed in the presence of an aromatic hydrocarbon solvent, and
wherein the reaction is performed at 0° C. to 50° C.