Hydrochloric Acid → 2-(Isoquinolin-5-yl)propanoic acid

HRID 586023ノート

反応式

HRID 586023 の反応式
[CH:1]1[C:10]2[C:5](=[C:6]([CH:11]([CH3:17])[C:12]([O:14]CC)=[O:13])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.Cl>[OH-].[Na+]>[CH:1]1[C:10]2[C:5](=[C:6]([CH:11]([CH3:17])[C:12]([OH:14])=[O:13])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 11390565Ethyl 2-(5-isoquinolinyl)propanoate

生成物 1

HCID 223376382-(Isoquinolin-5-yl)propanoic acid

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

実験手順

Ethyl 2-(5-isoquinolinyl)propanoate (1.00 g, 4.36 mmol) was heated at 85° C. in NaOH (25%, 20 mL) for 1 hour. The mixture was allowed to cool to room temperature, acidified to around pH 1 with HCl, and concentrated to a dry residue. The solid was extracted with CHCl3:isopropyl alcohol (3:1, 50 mL×4). The extracts were combined, filtered, and the filtrate concentrated under reduced pressure to provide the title compound. MS (ESI+) m/z 202 (M+H)+; MS (ESI−) m/z 200 (M−H)−; 1H NMR (DMSO, 300 MHz) δ 1.42 (d, J 7.1, 3H), 4.01 (q, J 7.1, 1H), 7.58 (t, J 8.1, 1H), 7.63 (d, J 7.5, 1H), 7.86 (d, J 8.1, 1H), 8.19 (d, J 6.8, 1H), 8.43 (d, J 6.8, 1H), 9.22 (s, 1H); Anal. Calcd for C12H10NO2Na+0.9H2O: C, 60.20; H, 4.97; N, 5.85. Found: C, 60.45; H, 5.26; N, 5.46.

後処理

  1. concentrationconcentrated to a dry residue
  2. extractionThe solid was extracted with CHCl3:isopropyl alcohol (3:1, 50 mL×4)
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure

出典と根拠

ORDレコード
ord-4c389e2f9b6d4dfc90b2e5c31a985142
出典データセット
uspto-grants-2005_08
特許番号
US06933311B2

反応ノート

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