Hydrochloric Acid → HCID 178474271、化合物

HRID 2398764ノート

反応式

HRID 2398764 の反応式
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([N+:12]([O-])=O)[CH:6]=1)(=[O:3])[CH3:2].Cl.Cl.C(NC1C=CC(O)=C(N)C=1)(=O)C.[C:29]([C:32]1[C:33](=[O:43])[O:34][C:35]([OH:42])=[C:36]([C:39](=O)[CH3:40])[C:37]=1[OH:38])(=[O:31])[CH3:30].C(=O)(O)[O-].[Na+]>O.[Pd].CO.C(O)C>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([NH:12][C:39](=[C:36]2[C:37]([OH:38])=[C:32]([C:29](=[O:31])[CH3:30])[C:33](=[O:43])[O:34][C:35]2=[O:42])[CH3:40])[CH:6]=1)(=[O:3])[CH3:2]

参加物

10

反応物 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 3322389N-(4-Hydroxy-3-nitrophenyl)acetamideHCID 21434080HCID 21434080、化合物HCID 1354659693,5-Diacetyl-2,6-dihydroxy-4h-pyran-4-one

生成物 1

HCID 178474271HCID 178474271、化合物

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

Following the procedures of Example 1, 4.0 g. (0.0204 mol) of 4-acetamido-2-nitrophenol (prepared by acetylation of the corresponding amine) is hydrogenated in a mixture of 150 ml. of ethanol, 3.3 ml. of concentrated hydrochloric acid and 0.5 g. of 10% palladium-on-carbon in a Parr apparatus at room temperature. Filtration of the reaction mixture gives a powder which is dissolved in a minimum amount of water and filtered. This aqueous solution of 4-acetamido-2-aminophenol hydrochloride is added to a mixture of 3,5-diacetyl-4,6-dihydroxy-2H-pyran-2-one (3.42 g., 0.0162 mol) and 1.36 g. (0.0162 mol) of sodium bicarbonate in 130 ml. of methanol. After 18 hours at reflux, the reaction mixture is filtered and the solid is recrystallized from dioxane-acetonitrile to give 3-[1-(5-acetamido-2-hydroxyphenylamino)ethylidene]-5-acetyl-4-hydroxy-2H-pyran-2,6(3H)-dione, m.p. 253°-254° C. (dec.).

後処理

  1. additionis hydrogenated in a mixture of 150 ml
  2. customat room temperature
  3. filtrationFiltration of the reaction mixture
  4. customgives a powder which
  5. filtrationfiltered
  6. temperatureAfter 18 hours at reflux
  7. filtrationthe reaction mixture is filtered
  8. customthe solid is recrystallized from dioxane-acetonitrile

出典と根拠

ORDレコード
ord-da41766049cf466b83cda1f24a33c683
出典データセット
uspto-grants-1977_05
特許番号
US04025642

反応ノート

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