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

HRID 2202524노트

반응식

HRID 2202524 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f1124ccc9c9f4eb5a5e88e7752eef235
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365552B2

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