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

HRID 1199549ノート

反応式

HRID 1199549 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 14797Potassium Hydroxide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-21a3d55f38554728b278d66a34fdad28
出典データセット
uspto-grants-1990_02
特許番号
US04900837

反応ノート

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