4-Methyl-3-nitroaniline → N-(4-methyl-3-nitrophenyl)cyclopropanecarboxamide

HRID 1921285

反応式

HRID 1921285 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH:12]1([C:15](O)=[O:16])[CH2:14][CH2:13]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:15]([CH:12]2[CH2:14][CH2:13]2)=[O:16])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

参加物

7

反応物 4

HCID 83904-Methyl-3-nitroanilineHCID 15655Cyclopropanecarboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 4104437N-(4-methyl-3-nitrophenyl)cyclopropanecarboxamide収率 93.9%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (4-methyl-3-nitrophenyl)amine (304 mg) in DMF (3 mL) were added cyclopropanecarboxylic acid (258 mg), HATU (1.14 g) and iPr2NEt (1.55 g) successively, and the mixture was stirred at room temperature for 16 hr under a nitrogen atmosphere. The reaction mixture was diluted with EtOAc (15 mL) and the resulted mixture was washed with 1 M HCl (15 mL×2), saturated aqueous NaHCO3 (15 mL×2) and brine, dried over MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with EtOAc-hexane (1:2) to give N-(4-methyl-3-nitrophenyl)cyclopropanecarboxamide (413 mg).

後処理

  1. washthe resulted mixture was washed with 1 M HCl (15 mL×2), saturated aqueous NaHCO3 (15 mL×2) and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with EtOAc-hexane (1:2)

出典と根拠

ORDレコード
ord-bca658655c604b3d9c42e3007194f17b
出典データセット
uspto-grants-2012_05
特許番号
US08173684B2

関連ノート

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