2-(Chloromethyl)quinoline → HCID 11725870、化合物

HRID 248177

反応式

HRID 248177 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH:12]([CH3:16])[C:13]([OH:15])=[O:14])[CH:6]=[CH:5]2.C[O-].[Na+].Cl[CH2:21][C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=1>CO>[CH3:16][CH:12]([C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([O:1][CH2:21][C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=3)[CH:3]=2)[CH:8]=1)[C:13]([OH:15])=[O:14]

参加物

5

反応物 3

HCID 203942-(Chloromethyl)quinolineHCID 162920DesmethylnaproxenHCID 10942334Sodium Methoxide

生成物 1

HCID 11725870HCID 11725870、化合物収率 151.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 6-hydroxy-α-methyl-2-naphthaleneacetic acid (10.8 g, 50 mmol) in methanol (100 ml) is added sodium methoxide (100 mmol). After 10 minutes the solvent is removed and replaced with dimethylformamide (250 ml). 2-(Chloromethyl)quinoline (17.8 g, 100 mmol) is then added and the reaction mixture is stirred for 8 days at room temperature. The reaction mixture is partitioned between water and methylene chloride, the organic layer is washed with water and evaporated to yield 27 g of an oil. Recrystallization of this oil twice from acetonitrile gives 10.6 g of white crystals of intermediate ether ester (42% yield, m.p. 106°-108° C.).

後処理

  1. customAfter 10 minutes the solvent is removed
  2. customThe reaction mixture is partitioned between water and methylene chloride
  3. washthe organic layer is washed with water
  4. customevaporated

出典と根拠

ORDレコード
ord-aaa6707d54f14cdf803fde042812c2cf
出典データセット
uspto-grants-1993_05
特許番号
US05208344

関連ノート

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