Sodium Hydroxide → 5-Cyano-6-methoxy-4-methylpicolinic acid

HRID 42493ノート

反応式

HRID 42493 の反応式
[C:1]([C:3]1[C:4]([CH3:16])=[CH:5][C:6]([C:11]([O:13]CC)=[O:12])=[N:7][C:8]=1[O:9][CH3:10])#[N:2].[OH-].[Na+]>CO.C1COCC1>[C:1]([C:3]1[C:4]([CH3:16])=[CH:5][C:6]([C:11]([OH:13])=[O:12])=[N:7][C:8]=1[O:9][CH3:10])#[N:2]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 67466404Ethyl 5-cyano-6-methoxy-4-methylpicolinate

生成物 1

HCID 674675275-Cyano-6-methoxy-4-methylpicolinic acid収率 87%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To a stirred solution of ethyl 5-cyano-6-methoxy-4-methylpicolinate (1.0 g, 4.54 mmol) in MeOH (30 mL) and THF (10 mL) was added 6N NaOH (2 mL, 12.00 mmol). The suspension was heated to 60° C. and stirred for 2 hr. (The reaction cleared up right away.) LCMS indicated that the reaction was complete. The reaction was cooled to RT and concentrated to near dryness. The slurry was neutralized with 6N HCl (2 mL) diluted with water, filtered, washed with water and dried under vacuum to give the product 5-cyano-6-methoxy-4-methylpicolinic acid (0.76 g, 3.95 mmol, 87% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 13.65 (br. s., 1H), 7.73 (s, 1H), 4.03 (s, 3H), 2.54 (s, 3H). MS (ES)+m/e 192.9 [M+H]+.

後処理

  1. temperatureThe reaction was cooled to RT
  2. concentrationconcentrated
  3. additiondiluted with water
  4. filtrationfiltered
  5. washwashed with water
  6. customdried under vacuum

出典と根拠

ORDレコード
ord-5b6fafb1b1ad4d65bff553ca57360e26
出典データセット
uspto-grants-2013_09
特許番号
US08536179B2

反応ノート

読み込み中…