Potassium Hydroxide → 1-(Methylamino)isoquinoline-6-carboxylic acid

HRID 880990노트

반응식

HRID 880990 반응식
[CH3:1][NH:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15]CC)=[O:14])=[CH:10][CH:11]=2)[CH:6]=[CH:5][N:4]=1.[OH-].[K+]>C(O)C>[CH3:1][NH:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([OH:15])=[O:14])=[CH:10][CH:11]=2)[CH:6]=[CH:5][N:4]=1

참가 물질

4

반응물 2

HCID 14797Potassium HydroxideHCID 67491629Ethyl 1-(methylamino)isoquinoline-6-carboxylate

생성물 1

HCID 674916261-(Methylamino)isoquinoline-6-carboxylic acid수율 72.3%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
65 °C

실험 절차

To a suspension of ethyl 1-(methylamino)isoquinoline-6-carboxylate (150 mg, 0.65 mmol) in ethanol (2.5 mL) was added 1 N aqueous potassium hydroxide (6.5 mL, 6.5 mmol). The reaction was heated to 65° C. for 1.5 hours. The reaction was cooled to room temperature and concentrated to dryness. The solid was dissolved in water and the solution was acidified with 1 N HCl. The mixture was concentrated. The solid was dissolved in water (50 mL) and extracted twice with 2-butanol (50 mL). The combined organics were washed with brine (20 mL), dried over magnesium sulfate, filtered, and concentrated to give the title compound (95 mg, 72%) as a white solid. +ESI (M+H) 203.2; 1H NMR (400 MHz, DMSO-d6, δ): 13.07 (br.s., 1H), 10.25 (d, J=4.9 Hz, 1H), 8.74 (d, J=8.8 Hz, 1H), 8.51 (s, 1H), 8.15 (dd, J=8.6, 1.8 Hz, 1H), 7.67 (d, J=6.8 Hz, 1H), 7.35 (d, J=7.0 Hz, 1H), 3.15 (d, J=4.7 Hz, 3H).

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated to dryness
  3. dissolutionThe solid was dissolved in water
  4. concentrationThe mixture was concentrated
  5. dissolutionThe solid was dissolved in water (50 mL)
  6. extractionextracted twice with 2-butanol (50 mL)
  7. washThe combined organics were washed with brine (20 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-64f11b2cef774a998de6188c2b572247
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993586B2

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