Lithium Hydroxide → 1-Hydroxyisoquinoline-6-carboxylic acid

HRID 1892574ノート

反応式

HRID 1892574 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 582525541-Hydroxyisoquinoline-6-carboxylic acid収率 48%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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), 824 (d, 2H), 7.93 (d, 1H), 7.22 (d, 1H), 6.88 (d, 1H).

後処理

  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

出典と根拠

ORDレコード
ord-153921e76be24673ad79c2b7fc404308
出典データセット
uspto-grants-2013_08
特許番号
US08507681B2

反応ノート

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