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

HRID 880990ノート

反応式

HRID 880990 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 674916261-(Methylamino)isoquinoline-6-carboxylic acid収率 72.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
65 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-64f11b2cef774a998de6188c2b572247
出典データセット
uspto-grants-2015_03
特許番号
US08993586B2

反応ノート

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