Nitric Acid → HCID 21506794、化合物

HRID 1287859ノート

反応式

HRID 1287859 の反応式
[NH:1]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]2([C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[CH2:9][CH2:8]2)[C:2]1=[O:18].[N+:19]([O-])([OH:21])=[O:20]>>[N+:19]([C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[C:3]1([CH2:4][CH2:5][C:6](=[O:7])[NH:1][C:2]1=[O:18])[CH2:8][CH2:9][C:10]2=[O:17])([O-:21])=[O:20]

参加物

3

反応物 2

HCID 944Nitric AcidHCID 17928Alonimid

生成物 1

HCID 21506794HCID 21506794、化合物

反応条件

温度
0 °C

実験手順

A total of 14.1 grams (0.06 M) of 2,3-dihydrospiro-[naphthalene-1(4H),3'-piperidine]-2',4,6'-trione was added in small portions to 100 milliliters of nitric acid (d = 1.4) cooled to -5° to -10° C. This temperature was maintained for 15 minutes and then allowed to warm to 0° C. The reaction mixture was poured into an ice-water mixture and filtered. The precipitate was recrystallized from aqueous acetone and then from acetic acid and then from an acetone-isopropyl alcohol-ethyl acetate mixture. Recrystallization from dioxane followed by chromatrographic purification from a silica gel column (eluted by dioxane) gave 2,3-dihydro-6-nitrospiro-[naphthalene-1(4H),3'-piperidine]-2',4,6'-trione, melting point 273°-275° C.

後処理

  1. temperaturecooled to -5° to -10° C
  2. temperatureThis temperature was maintained for 15 minutes
  3. filtrationfiltered
  4. customThe precipitate was recrystallized from aqueous acetone
  5. customRecrystallization from dioxane
  6. customfollowed by chromatrographic purification from a silica gel column (eluted by dioxane)

出典と根拠

ORDレコード
ord-1a1fa45410ed4179b03f443318a1be34
出典データセット
uspto-grants-1976_10
特許番号
US03985888

反応ノート

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