Hydrochloric Acid → 2-Methyl-6-[3-(quinolin-2-ylmethoxy)-phenoxymethyl]-benzoic acid

HRID 892135노트

반응식

HRID 892135 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][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:15]=2)[C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+].Cl>C(O)C>[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][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:15]=2)[C:3]=1[C:4]([OH:6])=[O:5]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22241476Methyl 2-methyl-6-[3-(quinolin-2-ylmethoxy)-phenoxymethyl]-benzoate

생성물 1

HCID 98010622-Methyl-6-[3-(quinolin-2-ylmethoxy)-phenoxymethyl]-benzoic acid

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of methyl 2-methyl-6-[3-(quinolin-2-ylmethoxy)-phenoxymethyl]-benzoate (1.6 g, 3.8 mmol, example 4) in ethanol (25 mL) is heated with a 10N sodium hydroxide solution (4.0 mL, 40 mmol) at 70° C. for 14 h. The reaction is cooled, neutralized with a 2N HCl solution (20 mL) and concentrated to remove the ethanol. Ethyl acetate is added and washed with water. The aqueous layer is saturated with sodium chloride and back extracted with ethyl acetate. The organic layers are combined, dried over magnesium sulfate, filtered and concentrated to yield a crude solid. The solid is purified by column chromatography (silica, 5 to 10% methanol in dichloromethane) to provide the title compound. An analytically pure sample is prepared by recystallization from methanol: m.p. 167–168° C., 1H NMR (300 MHz, CDCl3)δ0.15 (d, 2H), 7.80 (d, 1H), 7.71 (t, 1H), 7.61–7.51 (m, 2H), 7.26–7.10 (m, 3H), 7.00 (t, 1H), 6.66 (s, 1H), 6.52 (d, 1H), 6.46 (d, 1H), 5.26 (s, 2H), 5.15 (s, 2H), 2.44 (s, 3H); MS (ESI) 400 (M+H)+.

후처리

  1. temperatureThe reaction is cooled
  2. concentrationconcentrated
  3. customto remove the ethanol
  4. additionEthyl acetate is added
  5. washwashed with water
  6. extractionback extracted with ethyl acetate
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto yield a crude solid
  11. customThe solid is purified by column chromatography (silica, 5 to 10% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-57bc8147fd3e439cb9f3fc9ae236da54
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07005440B1

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