Water → 1H-Pyrrole-2-carboxylic acid, 4-nitro-1-propyl-, ethyl ester

HRID 23156

反応式

HRID 23156 の反応式
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)=[O:5])[CH3:2].[CH3:14][CH2:15][O-].[Na+].[CH3:18]I.O>CCO.C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:18][CH2:15][CH3:14])[CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)=[O:5])[CH3:2]

参加物

7

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 242169Ethyl 4-Nitropyrrole-2-carboxylateHCID 2723922Sodium ethoxide

生成物 1

HCID 9040721H-Pyrrole-2-carboxylic acid, 4-nitro-1-propyl-, ethyl ester収率 77%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6212Chloroform溶媒

反応条件

温度
80 °C

実験手順

4-Nitro-1H-pyrrole-2-carboxylic acid ethyl ester (5 g) was dissolved in 50 ml of dry EtOH, 50 ml of 1M sodium ethylate was added followed with 10 ml of CH3I. The reaction mixture was heated at 80° C. for 4 hours, cooled down to room temperature and distributed between water and chloroform. The organic phase was washed with water, dried with sodium sulfate and evaporated. The residue was recrystallized from hexane to yield 4.72 g (77%) of 1-propyl-4-nitro-1H-pyrrole-2-carboxylic acid ethyl ester 232. H1-NMR (DMSO-d6): 0.79 (t, 3H, CH3), 1.25 (t, 3H, CH3), 1.68 (m, 2H, CH2), 4.17-4.28 (m, 4H, 2CH2), 7.23 and 8.24 (d, 1H, pyrrole)

後処理

  1. temperaturecooled down to room temperature
  2. washThe organic phase was washed with water
  3. dry with materialdried with sodium sulfate
  4. customevaporated
  5. customThe residue was recrystallized from hexane

出典と根拠

ORDレコード
ord-fd07c35c22c94de7a7c4d8b98aa27f07
出典データセット
uspto-grants-2005_02
特許番号
US06849713B2

関連ノート

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