2-(Chloromethyl)quinoline → HCID 11725870, 화합물

HRID 248177

반응식

HRID 248177 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 11725870HCID 11725870, 화합물수율 151.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-aaa6707d54f14cdf803fde042812c2cf
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05208344

연결된 노트

불러오는 중…