Sodium Carbonate → 3-Isoquinolinecarboxylic acid, 4-hydroxy-1-methyl-7-phenoxy-, methyl ester

HRID 334449

반응식

HRID 334449 반응식
C(O[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]=2)[C:9]([OH:23])=[C:8]([C:24]([O:26][CH3:27])=[O:25])[N:7]=1)(=O)C.C([O-])([O-])=O.[Na+].[Na+]>[Pd].C(OCC)(=O)C>[OH:23][C:9]1[C:10]2[C:15](=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][CH:11]=2)[C:6]([CH3:5])=[N:7][C:8]=1[C:24]([O:26][CH3:27])=[O:25]

참가 물질

5

반응물 2

HCID 10340Sodium CarbonateHCID 86709145Methyl 1-(acetoxymethyl)-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

생성물 1

HCID 712448953-Isoquinolinecarboxylic acid, 4-hydroxy-1-methyl-7-phenoxy-, methyl ester수율 90%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

A reactor was charged with 1c (16.0 g), Pd/C (2.08 g), anhydrous Na2CO3 (2.56 g) and ethyl acetate (120 mL). The flask was vacuum-purged with nitrogen (3×) and vacuum-purged with hydrogen (3×). The flask was then pressurized with hydrogen and stirred at about 60° C. until completion of reaction. The flask was cooled to 20-25° C., the pressure released to ambient, the head space purged with nitrogen three times and mixture was filtered. The filtrate was concentrated. Methanol was added. The mixture was stirred and then cooled. Product precipitated and was filtered and dried in an oven (Yield: 90%, HPLC: 99.7%).

후처리

  1. customThe flask was vacuum-purged with nitrogen (3×)
  2. customvacuum-purged with hydrogen (3×)
  3. temperatureThe flask was cooled to 20-25° C.
  4. customthe head space purged with nitrogen three times and mixture
  5. filtrationwas filtered
  6. concentrationThe filtrate was concentrated
  7. additionMethanol was added
  8. stirringThe mixture was stirred
  9. temperaturecooled
  10. customProduct precipitated
  11. filtrationwas filtered
  12. customdried in an oven (Yield: 90%, HPLC: 99.7%)

출처 및 근거

ORD 기록
ord-1102260c45194757ba9eac16c267533d
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883823B2

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