Water → [4-(4-Amino-phenyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester

HRID 1468351ノート

反応式

HRID 1468351 の反応式
[CH3:1][O:2][C:3](=[O:26])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:25])[CH:11]=2)[CH:6]=1.C1COCC1.[Cl-].[NH4+].O>CO.[Zn]>[CH3:1][O:2][C:3](=[O:26])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:25])[CH:11]=2)[CH:6]=1

参加物

7

反応物 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 86694943[6-Fluoro-3-methyl-4-(4-nitro-phenyl)-naphthalen-2-yl]-acetic acid methyl ester

生成物 1

HCID 86694944[4-(4-Amino-phenyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester収率 67.7%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 887Methanol溶媒

実験手順

To a suspension of [6-fluoro-3-methyl-4-(4-nitro-phenyl)-naphthalen-2-yl]-acetic acid methyl ester (190 mg, 0.54 mmol) in methanol (3 mL) was added THF (2 mL). Then, zinc dust (287.1 mg, 4.4 mmol), and ammonium chloride (287.8 mg, 5.38 mmol) were added followed by water (1.3 mL). The reaction mixture was stirred at room temperature for 30 minutes. Solid was filtered and washed with ethyl acetate (20 mL). The solution was concentrated to remove organic solvent, and then diluted with water (25 mL). The mixture was extracted with ethyl acetate (2×20 mL). The combined organic extracts were washed with brine solution (30 mL) and dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration of the solvent under vacuum gave [4-(4-amino-phenyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (118 mg, 67.7%) as a light brown solid. 1H NMR (300 MHz, CDCl3) δ ppm 7.71-7.83 (m, 1 H), 7.69 (s, 1 H), 7.27 (s, 1 H), 7.10-7.22 (m, 1 H), 6.93-7.09 (m, 3 H), 6.83 (d, J=7.8 Hz, 1H), 3.86 (s, 2 H), 3.78 (br. s, 2 H), 3.74 (s, 3 H), 2.19 (s, 3 H). HRMS calcd. for C20H19FNO2 [(M+H)+] 324.1395, obsd. 324.1392.

後処理

  1. filtrationSolid was filtered
  2. washwashed with ethyl acetate (20 mL)
  3. concentrationThe solution was concentrated
  4. customto remove organic solvent
  5. additiondiluted with water (25 mL)
  6. extractionThe mixture was extracted with ethyl acetate (2×20 mL)
  7. washThe combined organic extracts were washed with brine solution (30 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationFiltration of the drying agent and concentration of the solvent under vacuum

出典と根拠

ORDレコード
ord-5dfaf107dd324032abfdff3d8d3b6e40
出典データセット
uspto-grants-2015_04
特許番号
US09000044B2

反応ノート

読み込み中…