Lithium Hydroxide → 1-Hydroxyisoquinoline-6-carboxylic acid

HRID 2064230노트

반응식

HRID 2064230 반응식
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14]C)=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][NH:3]1.O1CCCC1.[OH-].[Li+]>O>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][NH:3]1

참가 물질

5

반응물 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 42609191Methyl 1-oxo-1,2-dihydroisoquinoline-6-carboxylate

생성물 1

HCID 582525541-Hydroxyisoquinoline-6-carboxylic acid수율 48%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a mixture of methyl 1-oxo-1,2-dihydroisoquinoline-6-carboxylate (25 g, 0.133 mol), tetrahydrofuran (200 mL) and water (200 mL) was added lithium hydroxide (16.8 g, 0.40 mol) at room temperature, and the mixture was stirred for four hours. Thin layer chromatography (petroleum ether/ethyl acetate=1:1) indicated the reaction was complete. The reaction mixture was extracted with ethyl acetate (100 mL×3) to remove impurities. The aqueous layer was acidified with 4 N aqueous HCl to pH 5 and filtered. The solid was dried in vacuum to give 1-oxo-1,2-dihydroisoquinoline-6-carboxylic acid (11.3 g, 48%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.48 (s, 1H), 8.24 (d, 2H), 7.93 (d, 1H), 7.22 (d, 1H), 6.68 (d, 1H).

후처리

  1. extractionThe reaction mixture was extracted with ethyl acetate (100 mL×3)
  2. customto remove impurities
  3. filtrationfiltered
  4. customThe solid was dried in vacuum

출처 및 근거

ORD 기록
ord-9ca28a39ccb74372bab78e3513625ca8
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288405B2

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