3-Nitro-2(1H)-pyridinone → 5-Amino-1-methyl[3,4'-bipyridin]-6(1H)-one

HRID 28252ノート

反応式

HRID 28252 の反応式
[CH3:1][N:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[CH:5]=[C:4]([N+:14]([O-])=O)[C:3]1=[O:17].[N+](C1C(=O)NC=CC=1)([O-])=O>CN(C)C=O>[NH2:14][C:4]1[C:3](=[O:17])[N:2]([CH3:1])[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=2)[CH:5]=1

参加物

4

反応物 2

HCID 227933-Nitro-2(1H)-pyridinoneHCID 13386650HCID 13386650、化合物

生成物 1

HCID 233398285-Amino-1-methyl[3,4'-bipyridin]-6(1H)-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture containing 10.7 g. of 1-methyl-3-nitro-5-(4-pyridinyl)-2(1H)-pyridinone and 200 ml. of dimethylformamide was warmed to dissolve the nitro-pyridinone and the solution was filtered through infusorial earth. The filtrate was charged into a 500 ml. Parr bottle with 1.2 g. of 10% palladium-on-charcoal catalyst and the mixture was shaken under 40 p.s.i. of hydrogen at room temperature for three hours, after which time no further hydrogen was taken up. The reaction mixture was filtered and the filtrate was concentrated to dryness under reduced pressure (0.1 mm.) on a water bath at 40° C. leaving 10.1 g. of brown crystalline solid. The solid was recrystallized three times from benzene-ethanol, the third time using decolorizing charcoal, to yield 4.5 g. of 3-amino-1-methyl-5-(4-pyridinyl)-2(1H)-pyridinone, m.p. 175°-176° C. after drying at room temperature in vacuo for twenty hours.

後処理

  1. additionA mixture containing 10.7 g
  2. filtrationthe solution was filtered through infusorial earth
  3. additionThe filtrate was charged into a 500 ml
  4. filtrationThe reaction mixture was filtered
  5. concentrationthe filtrate was concentrated to dryness under reduced pressure (0.1 mm.) on a water bath at 40° C.
  6. customleaving 10.1 g
  7. customThe solid was recrystallized three times from benzene-ethanol
  8. customto yield 4.5 g
  9. dry with materialof 3-amino-1-methyl-5-(4-pyridinyl)-2(1H)-pyridinone, m.p. 175°-176° C. after drying at room temperature in vacuo for twenty hours

出典と根拠

ORDレコード
ord-d4df906ef473473a8e3b7653f453521a
出典データセット
uspto-grants-1980_09
特許番号
US04225715

反応ノート

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