5-(1H-pyrazol-1-yl)-1,6-naphthyridin-2(1H)-one → 5-hydrazino-1,6-naphthyridin-2(1H)-one

HRID 2309814ノート

反応式

HRID 2309814 の反応式
[N:1]1([C:6]2[N:15]=[CH:14][CH:13]=[C:12]3[C:7]=2[CH:8]=[CH:9][C:10](=[O:16])[NH:11]3)C=CC=[N:2]1.O.Cl.N(C1N=CC=C2C=1C=CC(=O)N2)N.C[O-].[Na+]>CO>[NH:1]([C:6]1[N:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10](=[O:16])[NH:11]2)[NH2:2]

参加物

5

反応物 3

HCID 103308045-(1H-pyrazol-1-yl)-1,6-naphthyridin-2(1H)-oneHCID 10942334Sodium MethoxideHCID 201565215-hydrazino-1,6-naphthyridin-2(1H)-one monohydrochloride monohydrate

生成物 1

HCID 138244945-hydrazino-1,6-naphthyridin-2(1H)-one

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

5-(1H-pyrazol-1-yl)-1,6-naphthyridin-2(1H)-one. To a mixture containing 5-hydrazino-1,6-naphthyridin-2(1H)-one monohydrochloride monohydrate suspended in 100 ml of methanol was added 1.35 g of sodium methoxide and the mixture stirred at room temperature for 20 minutes and then stripped to dryness in vacuo to produce 5-hydrazino-1,6-naphthyridin-2(1H)-one in free base form. To the residue was added 6.15 g of 1,1,3,3-tetramethoxypropane and 25 ml of ethylene glycol; and, the resulting mixture was heated with stirring to about 170° C., allowing the methanol boil off from the reaction mixture. The reaction mixture was allowed to stand at room temperature over the weekend and was then concentrated on a rotary evaporator. The residue was slurried in boiling methanol; and, the mixture was cooled and filtered. The solid was slurried in water, collected and dried in a vacuum oven at about 90° C. The solid was dissolved in boiling dimethylformamide, the hot solution treated. with decolorizing charcoal and filtered, and, the filtrate allowed to cool. The separated product was collected, washed with methanol and dried in a vacuum oven at 90° C. to yield 2.8 g of 5-(1H-pyrazol-1-yl)-1,6-naphthyridin-2(1H)-one, m.p. >300° C.

出典と根拠

ORDレコード
ord-7676f97241d548778c582d217ac60347
出典データセット
uspto-grants-1987_09
特許番号
US04697021

反応ノート

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