Water → N-(2-Methoxy-6-nitrophenyl)valeroamide

HRID 1655468

反応式

HRID 1655468 の反応式
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:4]=1[NH2:5].S(=O)(=O)(O)O.[OH2:18].[OH-].[Na+]>C(OC(=O)CCCC)(=O)CCCC>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:4]=1[NH:5][C:6](=[O:18])[CH2:4][CH2:3][CH2:9][CH3:8]

参加物

6

反応物 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 854916-Nitro-o-anisidine

生成物 1

HCID 19792196N-(2-Methoxy-6-nitrophenyl)valeroamide収率 36%

試薬・触媒・溶媒 1

HCID 74959Valeric anhydride溶媒

反応条件

温度
135 °C

実験手順

To a mixture of 2-methoxy-6-nitroaniline (5.9 g) in valeric anhydride (14 g) was added a catalytic amount of conc. sulfuric acid, which was stirred for 1.5 hour at 130-140° C. To the reaction mixture was added water, which was made basic with 6N NaOH. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and dried. The solvent was distilled off. The residue was purified by column chromatography on silica gel. Crude crystals thus obtained were recrystallized from ethyl acetate-hexane to give colorless crystals (3.2 g, 36%), m.p. 113-114° C.

後処理

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. distillationThe solvent was distilled off
  5. customThe residue was purified by column chromatography on silica gel
  6. customCrude crystals thus obtained
  7. customwere recrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-f84da17371ff45758fada74d8c615686
出典データセット
uspto-grants-1993_10
特許番号
US05250554

関連ノート

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