Nitric Acid → 3-Methoxy-2-methyl-4-nitropyridine 1-oxide

HRID 845540

反応式

HRID 845540 の反応式
[N+:1]([O-:4])(O)=[O:2].[CH3:5][O:6][C:7]1[C:8]([CH3:14])=[N+:9]([O-:13])[CH:10]=[CH:11][CH:12]=1.[OH-].[Na+]>C(O)(=O)C>[CH3:5][O:6][C:7]1[C:8]([CH3:14])=[N+:9]([O-:13])[CH:10]=[CH:11][C:12]=1[N+:1]([O-:4])=[O:2]

参加物

5

反応物 3

HCID 944Nitric Acid2 回HCID 14798Sodium HydroxideHCID 122140163-Methoxy-2-methylpyridine 1-oxide

生成物 1

HCID 151634563-Methoxy-2-methyl-4-nitropyridine 1-oxide

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

8 ml of concentrated nitric acid are added in four portions of 2 ml each to 5.4 g of 3-methoxy-2-methylpyridine 1-oxide in 12 ml of glacial acetic acid at 80° C. in the course of 6 hours, the mixture is stirred at the same temperature overnight, a further 8 ml of nitric acid are added in three portions in the course of 6 hours and the mixture is stirred for a further 15 hours. After cooling, the mixture is poured onto ice (40 g) and brought to pH 6 with 10N sodium hydroxide solution, the byproduct (3-methoxy-2-methyl-4-nitropyridine) which has precipitated out is filtered off and the filtrate is extracted four times with 50 ml of methylene chloride. After drying, the combined organic phases are concentrated completely and the residue is recrystallized from a little methylene chloride/petroleum ether. 4.2 g (57% of theory) of the title compound are obtained in the form of yellow crystals of m.p. 103°-104° C.

後処理

  1. stirringthe mixture is stirred for a further 15 hours
  2. temperatureAfter cooling
  3. additionthe mixture is poured onto ice (40 g)
  4. customthe byproduct (3-methoxy-2-methyl-4-nitropyridine) which has precipitated out
  5. filtrationis filtered off
  6. extractionthe filtrate is extracted four times with 50 ml of methylene chloride
  7. customAfter drying
  8. concentrationthe combined organic phases are concentrated completely
  9. customthe residue is recrystallized from a little methylene chloride/petroleum ether

出典と根拠

ORDレコード
ord-05dccb811414497daa08be9fb4079333
出典データセット
uspto-grants-1988_07
特許番号
US04758579

関連ノート

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