Sulfuric Acid → 2-(4-Tert-butyl-benzoylamino)-4-hydroxy-benzoic acid methyl ester

HRID 1392261

반응식

HRID 1392261 반응식
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7](N)=[CH:6][C:5]=1[NH:11][C:12](=[O:23])[C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=1.N([O-])=[O:26].[Na+].OS(O)(=O)=O>FC(F)(F)C(O)=O.O>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([OH:26])=[CH:6][C:5]=1[NH:11][C:12](=[O:23])[C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=1

참가 물질

6

반응물 3

HCID 1118Sulfuric AcidHCID 23668193Sodium NitriteHCID 691966714-Amino-2-(4-tert-butyl-benzoylamino)-benzoic acid methyl ester

생성물 1

HCID 691962732-(4-Tert-butyl-benzoylamino)-4-hydroxy-benzoic acid methyl ester수율 71%

시약·촉매·용매 2

HCID 962Water용매HCID 6422Trifluoroacetic acid용매

실험 절차

To a solution of afford 4-amino-2-(4-tert-butyl-benzoylamino)-benzoic acid methyl ester (0.711 g, 2.18 mmol) in trifluoroacetic acid cooled to 0° C. was added NaNO2 (0.182 g, 2.64 mmol, 1.21 eq) as a solution in water (4 mL) and the reaction was stirred 5 minutes. It was then added dropwise to 30% solution of H2SO4 (50 mL) at 65° C. and stirred for 15 minutes. It was extracted with ethyl acetate, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/hexanes (20/80) to afford 2-(4-tert-butyl-benzoylamino)-4-hydroxy-benzoic acid methyl ester (0.508, 71%) as a white solid. mp=146.0-148.4° C.; mass spectrum (−ES, M−H) m/z 326. 1H NMR (400 MHz, DMSO-d6); δ 11.95 (bs, 1H), 10.60 (bs, 1H), 8.26 (d, 1H), 7.88 (m, 3H), 7.62 (d, 2H), 6.58 (dd, 1H), 3.85 (s, 3H), 1.32 (s, 9H). Elemental analysis: Calcd. for C19H21NO4: C, 69.71; H, 6.47; N, 4.28. Found: C, 69.20; H, 6.54; N, 4.17.

후처리

  1. stirringstirred for 15 minutes
  2. extractionIt was extracted with ethyl acetate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-9ffa27713b6c4f3c880427eb8b965121
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07342039B2

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