Glycine → 2,3-Dihydroxyquinoxaline

HRID 439415

반응식

HRID 439415 반응식
NCC(O)=O.[C:6]([O:13]CC)(=O)[C:7]([O:9]CC)=O.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH2:23].C(O)(=O)C(O)=O.OS(O)(=O)=O.OP(O)(O)=O>Cl>[NH:16]1[C:17]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:23][C:6](=[O:13])[C:7]1=[O:9]

참가 물질

8

반응물 6

HCID 750GlycineHCID 971Oxalic Acid2회HCID 1004Phosphoric AcidHCID 1118Sulfuric AcidHCID 7243O-PhenylenediamineHCID 7268Diethyl Oxalate

생성물 1

HCID 274912,3-Dihydroxyquinoxaline

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매2회

실험 절차

The compounds synthesized for testing as potential glycine antagonists which are not substituted on the amide (1 or 4) position are summarized below (Table I). Most were available by simple condensation of diethyl oxalate with the corresponding diaminobenzene according to Cheeseman, G. W. H., J. Chem. Soc. 1171 (1962). The 1,4-dihydro-2,3-quinoxalinediones may be easily prepared in high yield by heating oxalic acid and the corresponding o-diamine to about 100° to 140° C. for 1 to 10 hr. in the presence of a strong mineral acid such as HCl, H2SO4, H3PO4 and the like. See, Mager and Berends, Rec. Trav. Chim. 77:842 (1958). In a preferred embodiment, oxalic acid and the o-diamine are heated to 125° C. in 2N HCl for 2.5 hours to give the corresponding 1,4-dihydro-2,3-quinoxalinedione in high yield.

후처리

  1. customin high yield

출처 및 근거

ORD 기록
ord-8fb154ed4043421580e163b213180e6f
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05514680

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