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Sodium Hydroxide → 4-Fluoro-2-methoxy-5-morpholin-4-yl-benzoic acid

HRID 457987
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HRID 457987 반응식
C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[C:7]([F:16])=[CH:6][C:5]=1[O:17][CH3:18].[OH-].[Na+]>C(O)C>[F:16][C:7]1[C:8]([N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)=[CH:9][C:4]([C:3]([OH:19])=[O:2])=[C:5]([O:17][CH3:18])[CH:6]=1
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참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 220934904-Fluoro-2-methoxy-5-morpholin-4-yl-benzoic acid methyl ester

생성물 1

HCID 184682204-Fluoro-2-methoxy-5-morpholin-4-yl-benzoic acid수율 79.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A suspension of 4-fluoro-2-methoxy-5-morpholin-4-yl-benzoic acid methyl ester (1.20 g, 4.46 mmol) in ethanol (22.0 mL) was treated with aq 2 N NaOH (13 mL, 26.7 mmol). The mixture was stirred at room temperature for 2 h, concentrated until most of the ethanol was removed and acidified with aq 2 N HCl to pH 1. After extracting with ethyl acetate, the organic layer was washed with saturated aq NaCl, dried over MgSO4 and concentrated to give-4-fluoro-2-methoxy-5-morpholin-4-yl-benzoic acid (0.90 g, 79%): 1H NMR (DMSO-d6 300 MHz) δ 12.62 (s, 1 H), 7.34 (d, J=10.5 Hz, 1 H), 7.04 (d, J=14.7 Hz, 1 H), 3.76 (s, 3 H), 3.70 (t, J=4.7 Hz, 4 H), 2.90 (t, J=4.7 Hz, 4 H).

후처리

  1. concentrationconcentrated until most of the ethanol
  2. customwas removed
  3. extractionAfter extracting with ethyl acetate
  4. washthe organic layer was washed with saturated aq NaCl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8f48ed1a73c84054b3526384a3f43b46
출처 데이터셋
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07189749B2

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