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

HRID 42493

반응식

HRID 42493 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

HCID 674675275-Cyano-6-methoxy-4-methylpicolinic acid수율 87%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-5b6fafb1b1ad4d65bff553ca57360e26
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536179B2

연결된 노트

불러오는 중…