Water → 4-Iodo-2-methoxypyridine-3-carboxylic acid

HRID 1034934

反応式

HRID 1034934 の反応式
[I:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([O:10][CH3:11])[N:5]=[CH:4][CH:3]=1.CC(=CC)C.O.Cl([O-])=[O:19].[Na+]>CC(O)(C)C>[I:1][C:2]1[C:7]([C:8]([OH:19])=[O:9])=[C:6]([O:10][CH3:11])[N:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 105532-Methyl-2-buteneHCID 100383814-Iodo-2-methoxynicotinaldehydeHCID 23668197Sodium Chlorite

生成物 1

HCID 184399404-Iodo-2-methoxypyridine-3-carboxylic acid

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

To a solution of 4-iodo-2-methoxynicotinaldehyde (1 g, 3.58 mmol) in t-BuOH (6 mL), cooled at 25° C., is added 2-methyl-2-butene (6 mL, 2 M solution), Na2HPO4 (1.2 g) and water (3 mL). The reaction mixture is stirred for 5 minutes and sodium chlorite (800 mg, 8.9 mmol) is added slowly. Stirring of the mixture is continued until the aldehyde is completely consumed (3 hours, monitored by LCMS). The reaction is quenched with aq. formic acid. The mixture is partitioned between ethyl acetate (100 mL) and the organic extracts are washed with brine, dried over Na2SO4, filtered and concentrated. The white powder was used for the next reaction without any further purification. 1H NMR 400 MHz (DMSO-d6) δ 10.06 (s, 1H), 7.89 (d, 1H, J=5.6 Hz), 7.48 (d, 1H, J=5.6 Hz), 3.87 (s, 1H); MS m/z 294.1 (M+1). MS m/z 280.01 (M+1).

後処理

  1. stirringStirring of the mixture
  2. customis completely consumed (3 hours, monitored by LCMS)
  3. customThe reaction is quenched with aq. formic acid
  4. customThe mixture is partitioned between ethyl acetate (100 mL)
  5. washthe organic extracts are washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe white powder was used for the next reaction without any further purification

出典と根拠

ORDレコード
ord-9a313dd65a38467894278503abdde5f1
出典データセット
uspto-grants-2013_10
特許番号
US08546370B2

関連ノート

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