Hydrochloric Acid → 5-Hydroxy-2-(2-methoxyethoxy)isonicotinaldehyde

HRID 1471727노트

반응식

HRID 1471727 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:8]([O:11]COC)=[CH:9][N:10]=1)[CH:6]=[O:7].Cl.[C:16]([O-])([O-])=[O:17].[K+].[K+].C1[CH2:26][O:25][CH2:24]C1>O>[OH:11][C:8]1[C:5]([CH:6]=[O:7])=[CH:4][C:3]([O:2][CH2:1][CH2:24][O:25][CH3:26])=[N:10][CH:9]=1.[OH:11][C:8]1[CH:9]=[N:10][C:3]([O:2][CH2:1][CH2:24][O:25][CH3:26])=[C:4]([CH:5]=1)[CH:16]=[O:17]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 121807202-Methoxy-5-(methoxymethoxy)-4-pyridinecarboxaldehyde

생성물 2

HCID 866907685-Hydroxy-2-(2-methoxyethoxy)isonicotinaldehyde수율 60%HCID 866907695-Hydroxy-2-(2-methoxyethoxy)nicotinaldehyde수율 11%

시약·촉매·용매 1

HCID 962Water용매

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온도
50 °C

실험 절차

To a solution of 2-methoxy-5-(methoxymethoxy)isonicotinaldehyde (1.27 g, 5.29 mol) in THF (5 mL) was added HCl (3 N, 4 mL). The reaction was stirred at 50° C. for 1 h, cooled to rt, and diluted with water (5 mL). The mixture was neutralized to pH 7-8 with solid K2CO3 and the aqueous layer was extracted with EtOAc (100 mL) twice. The combined organic layers were dried over Na2SO4, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes to give 5-hydroxy-2-(2-methoxyethoxy)isonicotinaldehyde (630 mg, 60%) and 5-hydroxy-2-(2-methoxyethoxy)nicotinaldehyde (120 mg, 11%). Data for 5-hydroxy-2-(2-methoxyethoxy)isonicotinaldehyde: 1H NMR (400 MHz, CDCl3) δ 9.98 (s, 1H), 9.50 (s, 1H), 8.07 (s, 1H), 7.02 (s, 1H), 4.51-4.39 (m, 2H), 3.81-3.72 (m, 2H), 3.47 (s, 3H). LRMS (M+H+) m/z 198.1. Data for and 5-hydroxy-2-(2-methoxyethoxy)nicotinaldehyde: 1H NMR (400 MHz, CDCl3) δ 10.3 (s, 1H), 7.99 (d, J=3.2 Hz, 1H), 7.58 (d, J=3.2 Hz, 1H), 7.18-7.07 (br, 1H), 4.54 (dd, J=5.4, 3.7 Hz, 2H), 3.84 (dd, J=5.4, 3.7 Hz, 2H), 3.49 (s, 3H). LRMS (M+H+) m/z 198.1

후처리

  1. temperaturecooled to rt
  2. extractionthe aqueous layer was extracted with EtOAc (100 mL) twice
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified on silica gel using
  6. additiona mixture of EtOAc and hexanes

출처 및 근거

ORD 기록
ord-31cd50aaf53649a882195a98a4445393
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012450B2

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