Sodium Hydroxide → 3-Amino-6-(2,4-dichloro-phenyl)-5-trifluoromethyl-pyridine-2-carboxylic acid

HRID 2202524ノート

反応式

HRID 2202524 の反応式
C[O:2][C:3]([C:5]1[C:10]([NH2:11])=[CH:9][C:8]([C:12]([F:15])([F:14])[F:13])=[C:7]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])[N:6]=1)=[O:4].[OH-].[Na+].O1CCOCC1>CO>[NH2:11][C:10]1[C:5]([C:3]([OH:4])=[O:2])=[N:6][C:7]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])=[C:8]([C:12]([F:13])([F:14])[F:15])[CH:9]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 673834083-Amino-6-(2,4-dichloro-phenyl)-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester

生成物 1

HCID 584423403-Amino-6-(2,4-dichloro-phenyl)-5-trifluoromethyl-pyridine-2-carboxylic acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

3-Amino-6-(2,4-dichloro-phenyl)-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (0.9 g, 2.465 mmol) was suspended in MeOH (15 ml) and NaOH 2M (2.465 ml, 4.93 mmol) was added under stirring. 1,4-Dioxane (15.00 ml) was added and the solution was left standing at RT over night. The solvent was removed in vacuo and the resulting residue was dissolved in water (10 ml) and carefully acidified to pH4 with slow addition of 2M HCl (2 ml) whilst stirring. The mixture was extracted with EtOAc (20 ml) and the organic portion was washed with brine and concentrated in vacuo. The residue was purified by reverse phase chromatography (130 g C18 column) eluting with water/MeOH to afford the title compound; LS-MS Rt=1.57 mins [M+H]+ 351.0 (Method 2minLC_v002).

後処理

  1. waitthe solution was left
  2. waitstanding at RT over night
  3. customThe solvent was removed in vacuo
  4. dissolutionthe resulting residue was dissolved in water (10 ml)
  5. additioncarefully acidified to pH4 with slow addition of 2M HCl (2 ml)
  6. stirringwhilst stirring
  7. extractionThe mixture was extracted with EtOAc (20 ml)
  8. washthe organic portion was washed with brine
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by reverse phase chromatography (130 g C18 column)
  11. washeluting with water/MeOH

出典と根拠

ORDレコード
ord-f1124ccc9c9f4eb5a5e88e7752eef235
出典データセット
uspto-grants-2016_06
特許番号
US09365552B2

反応ノート

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