Methyl iodide → N-(4-chlorobenzyl)-6-(hydroxymethyl)-8-iodo-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide

HRID 1264992ノート

反応式

HRID 1264992 の反応式
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([CH2:21][OH:22])=[CH:15][C:14]=3[I:23])=[O:9])=[CH:4][CH:3]=1.[C:26]([O-])([O-])=O.[K+].[K+].CI.CO.C(Cl)Cl>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[C:14]([I:23])[CH:15]=[C:16]([CH2:21][OH:22])[CH:17]=3)[N:12]([CH3:26])[CH:11]=2)=[O:9])=[CH:24][CH:25]=1

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21226129Dichloromethane methanolHCID 178522929HCID 178522929、化合物

生成物 1

HCID 22724554N-(4-chlorobenzyl)-6-(hydroxymethyl)-8-iodo-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide収率 54%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of N-(4-chlorobenzyl)-4-hydroxy-6-(hydroxymethyl)-8-iodo-3-quinolinecarboxamide(6.5 g) in anhydrous DMF (116.7 mL) is heated to 65° C. to solubilize the starting material. The solution is allowed to cool to room temperature. To this solution is added K2CO3 (7.68 g) and CH3I (8.65 mL). The reaction is stirred at room temperature overnight. The reaction is poured into H20 (1L) to precipitate the product. The solid is filtered, adsorbed onto silica, and chromatographed in 2 batches (eluent 100% CH2Cl2 (3L), 0.5% MeOH in CH2Cl2 (1L), and 1% MeOH in CH2Cl2 (9L)). Product-containing fractions are combined and condensed to afford 3.6 g (54%) of the desired product as a white solid.

後処理

  1. customto precipitate the product
  2. filtrationThe solid is filtered
  3. customchromatographed in 2 batches (eluent 100% CH2Cl2 (3L), 0.5% MeOH in CH2Cl2 (1L), and 1% MeOH in CH2Cl2 (9L))
  4. customcondensed

出典と根拠

ORDレコード
ord-89b127be896448f99475095110b208bc
出典データセット
uspto-grants-2003_04
特許番号
US06544990B2

反応ノート

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