Pyridine → 2-methoxy-5-[(E)-C-methyl-N-[(4-nitrophenyl)methoxy]carbonimidoyl]phenol

HRID 41926

反応式

HRID 41926 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([C:10](=O)[CH3:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Cl.[N+:14]([C:17]1[CH:25]=[CH:24][C:20]([CH2:21][O:22][NH2:23])=[CH:19][CH:18]=1)([O-:16])=[O:15].N1C=CC=CC=1>CCO>[N+:14]([C:17]1[CH:18]=[CH:19][C:20]([CH2:21][O:22]/[N:23]=[C:10](/[C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([OH:1])[CH:3]=2)\[CH3:11])=[CH:24][CH:25]=1)([O-:16])=[O:15]

参加物

5

反応物 3

HCID 1049PyridineHCID 74967Hydroxylamine, O-((4-nitrophenyl)methyl)-, hydrochloride (1:1)HCID 956931-(3-Hydroxy-4-methoxyphenyl)ethanone

生成物 1

HCID 885675852-methoxy-5-[(E)-C-methyl-N-[(4-nitrophenyl)methoxy]carbonimidoyl]phenol収率 89.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of ketone 12 (200 mg, 1.20 mmol) in EtOH (2.0 mL) was treated with compound 19 (0.27 g, 1.32 mmol) and pyridine (0.5 mL) and the resulting mixture heated at reflux for 3 h then cooled and the solvent evaporated under reduced pressure. The ensuing residue was partitioned between CH2Cl2 (10 mL) and H2O (10 mL). The separated aqueous fraction was extracted with CH2Cl2 (1×5.0 ml) and the combined organic fractions were dried (MgSO4) then filtered and concentrated under reduced pressure to give a light-yellow solid. Recrystallisation (isopropanol) of this material afforded the title compound CP30218 (340 mg, 89%) as pale-yellow crystals, m.p. 105.0-105.7° C.

後処理

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 3 h
  3. temperaturethen cooled
  4. customthe solvent evaporated under reduced pressure
  5. customThe ensuing residue was partitioned between CH2Cl2 (10 mL) and H2O (10 mL)
  6. extractionThe separated aqueous fraction was extracted with CH2Cl2 (1×5.0 ml)
  7. dry with materialthe combined organic fractions were dried (MgSO4)
  8. filtrationthen filtered
  9. concentrationconcentrated under reduced pressure
  10. customto give a light-yellow solid
  11. customRecrystallisation (isopropanol) of this material

出典と根拠

ORDレコード
ord-20d13991690f42f4b83fbf3c2b02462a
出典データセット
uspto-grants-2013_09
特許番号
US08536157B2

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