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

HRID 62392

反応式

HRID 62392 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-23e15ea44514410e8c7fa5e828852832
出典データセット
uspto-grants-2016_09
特許番号
US09446041B2

関連ノート

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