Sodium Hydroxide → 2-(1-Naphthalenyl)-6,7-methylenedioxyquinolin-4-one

HRID 38645

반응식

HRID 38645 반응식
[C:1]([C:4]1[C:5]([NH:13][C:14]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)=O)=[CH:6][C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1)(=[O:3])[CH3:2].[OH-].[Na+]>O1CCOCC1>[C:16]1([C:14]2[CH2:2][C:1](=[O:3])[C:4]3[C:5](=[CH:6][C:7]4[O:11][CH2:10][O:9][C:8]=4[CH:12]=3)[N:13]=2)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 926571N-(6-acetyl-1,3-benzodioxol-5-yl)naphthalene-1-carboxamide

생성물 1

HCID 666589682-(1-Naphthalenyl)-6,7-methylenedioxyquinolin-4-one

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

The synthetic procedure of target compounds 153 is illustrated in Scheme 11. The starting 2-amino-4,5-methylenedioxy-acetophenone (148) was first reacted with naphthalene-1-carbonyl chloride (149) to give N-(6-Acetyl-1,3-benzodioxol-5-yl)naphthalene-1-carboxamide (150). Then, the intermediate (150) was subjected to cyclization in dioxane, in the presence of NaOH, to afford 2-(1-Naphthalenyl)-6,7-methylenedioxyquinolin-4-one (151). Compound 151 was first reacted with tetrabenzylpyrophosphate in THF, in the presence of NaH, to yield Dibenzyl 2-(1-naphthalenyl)-6,7-methylenedioxyquinolin-4-yl Phosphate (152). Compound 152 was then subjected to catalytic hydrogenation in MeOH to give its diphosphoric acid (153).

출처 및 근거

ORD 기록
ord-f1b1195431e24f799d092f7a24a33738
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524740B2

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