4-Nitrobenzoic Acid → N-methoxy-N-methyl-4-nitrobenzamide

HRID 926465

反応式

HRID 926465 の反応式
C(N(CC)CC)C.[N+:8]([C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][CH:12]=1)([O-:10])=[O:9].Cl.[CH3:21][NH:22][O:23][CH3:24].CCN=C=NCCCN(C)C>C(Cl)Cl>[CH3:24][O:23][N:22]([CH3:21])[C:15](=[O:16])[C:14]1[CH:18]=[CH:19][C:11]([N+:8]([O-:10])=[O:9])=[CH:12][CH:13]=1

参加物

6

反応物 4

HCID 61084-Nitrobenzoic AcidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

生成物 1

HCID 2991007N-methoxy-N-methyl-4-nitrobenzamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Triethylamine (4.89 mL, 35.184 mmol) was added slowly to a mixture of commercially available 4-nitrobenzoic acid (3.0 g, 17.592 mmol), N,O-dimethylhydroxylamine hydrochloride (1.92 g, 19.351 mmol), and EDCI (4.05 g, 21.11 mmol) in CH2Cl2 (30 mL). The mixture was stirred at room temperature overnight then quenched with saturated aqueous NaHCO3. Water (50 mL) was added followed by additional CH2Cl2. The mixture as stirred for 10 minutes and layers were separated. The CH2Cl2 layer was dried over Na2SO4, then filtered. The solvent was removed under reduced pressure and the residual oil chromatographed (CH2Cl2/EtOAc) to provide the title compound as a white solid.

後処理

  1. customthen quenched with saturated aqueous NaHCO3
  2. additionWater (50 mL) was added
  3. stirringThe mixture as stirred for 10 minutes
  4. customlayers were separated
  5. dry with materialThe CH2Cl2 layer was dried over Na2SO4
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure
  8. customthe residual oil chromatographed (CH2Cl2/EtOAc)

出典と根拠

ORDレコード
ord-437639d7c4124a4e8cecdd347042b993
出典データセット
uspto-grants-2016_03
特許番号
US09284308B2

関連ノート

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