2-(1-Ethylpropyl)-6-methoxyisonicotinic acid methyl ester → 2-(1-Ethylpropyl)-6-methoxyisonicotinic acid

HRID 245080노트

반응식

HRID 245080 반응식
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[N:7]=[C:6]([CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[CH:5]=1>C(O)C.O.[OH-].[Na+]>[CH2:13]([CH:12]([C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([O:10][CH3:11])[N:7]=1)[C:3]([OH:17])=[O:2])[CH2:15][CH3:16])[CH3:14]

참가 물질

5

반응물 1

HCID 670268752-(1-Ethylpropyl)-6-methoxyisonicotinic acid methyl ester

생성물 1

HCID 584181082-(1-Ethylpropyl)-6-methoxyisonicotinic acid수율 85.3%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 14798Sodium Hydroxide용매

반응 조건

온도
70 °C

실험 절차

A solution of 2-(1-ethyl-propyl)-6-methoxy-isonicotinic acid methyl ester (50 g, 0.211 mol) in ethanol (250 mL), water (50 mL) and 32% aq. NaOH (50 mL) is stirred at 80° C. for 1 h. The mixture is concentrated and the residue is dissolved in water (200 mL) and extracted with TBME. The org. phase is separated and washed once with water (200 mL). The TBME phase is discarded. The combined aq. phases are acidified by adding 25% aq. HCl and then extracted with EA (400+200 mL). The combined org. extracts are concentrated. Water (550 mL) is added to the remaining residue. The mixture is heated to 70° C., cooled to rt and the precipitate that forms is collected and dried to give the title compound (40.2 g) as a white solid; LC-MS: tR=0.95 min, [M+1]+=224.04; 1H NMR (D6-DMSO): δ 0.73 (t, J=7.3 Hz, 6H), 1.59-1.72 (m, 4H), 2.52-2.58 (m, 1H), 3.88 (s, 3H), 7.00 (d, J=1.0 Hz, 1H), 7.20 (d, J=1.0 Hz, 1H).

후처리

  1. concentrationThe mixture is concentrated
  2. dissolutionthe residue is dissolved in water (200 mL)
  3. extractionextracted with TBME
  4. customphase is separated
  5. washwashed once with water (200 mL)
  6. additionby adding 25% aq. HCl
  7. extractionextracted with EA (400+200 mL)
  8. concentrationextracts are concentrated
  9. additionWater (550 mL) is added to the remaining residue
  10. temperaturecooled to rt
  11. customthe precipitate that forms is collected
  12. customdried

출처 및 근거

ORD 기록
ord-19308e688fc743f4b364ffb219359ebe
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658675B2

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