Hydrochloric Acid → 5-(Ethoxycarbonyl)pyridine-3-carboxylic acid

HRID 260183노트

반응식

HRID 260183 반응식
[N:1]1[CH:6]=[C:5]([C:7]([O:9]CC)=[O:8])[CH:4]=[C:3]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:2]=1.Cl>C(O)C.[OH-].[K+]>[C:12]([C:3]1[CH:4]=[C:5]([C:7]([OH:9])=[O:8])[CH:6]=[N:1][CH:2]=1)([O:14][CH2:15][CH3:16])=[O:13]

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 783403,5-Pyridinedicarboxylic acid, 3,5-diethyl ester

생성물 1

HCID 12144465-(Ethoxycarbonyl)pyridine-3-carboxylic acid

시약·촉매·용매 2

HCID 702Ethanol용매HCID 14797Potassium Hydroxide용매

실험 절차

To a solution of 10 g (0.045 mol) of diethyl 3,5-pyridinedicarboxylate in 75 ml of ethyl alcohol, 25 ml of 2N alcoholic KOH were added while stirring. Stirring was continued for 1/2 hour at room temperature. To the mixture, 12.5 ml of 4N HCl were added while stirring. The solid which separated was filtered and washed with alcohol. The combined filtrate and washings were distilled on rotovap and the residue was washed with water, filtered and crystallized from ethanol. Yield 7.5 g (86%), m.p. 180°-182° C., NMR (CDCl3 /DMSO-d6) δ 10.56 (bs, 1H, COOH), 9.26 (d, 2H, J=2 Hz, C2 and C6 pyridine protons), 8.75 (t, 1H, J-2 Hz, C4 pyridine protons), 4.4 (q, 2H, J=7 Hz, O--CH2), 1.42 (t, 3H, J=7 Hz, CH3).

후처리

  1. stirringStirring
  2. stirringwhile stirring
  3. customThe solid which separated
  4. filtrationwas filtered
  5. washwashed with alcohol
  6. distillationThe combined filtrate and washings were distilled on rotovap
  7. washthe residue was washed with water
  8. filtrationfiltered
  9. customcrystallized from ethanol

출처 및 근거

ORD 기록
ord-4d554e7f224d41c0af58a64f19103f26
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05525727

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