Sodium Hydroxide → 1-Cyano-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid

HRID 706218ノート

反応式

HRID 706218 の反応式
C[O:2][C:3]([C:5]1[N:6]=[C:7]([C:24]#[N:25])[C:8]2[C:13]([C:14]=1[O:15][CH3:16])=[CH:12][CH:11]=[CH:10][C:9]=2[O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:4].[OH-].[Na+]>CO.O1CCCC1>[C:24]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][C:9]=2[O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14]([O:15][CH3:16])=[C:5]([C:3]([OH:4])=[O:2])[N:6]=1)#[N:25]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 671104881-Cyano-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester

生成物 1

HCID 671101241-Cyano-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid収率 92.7%

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

To a mixture of 1-cyano-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester (727 mg, 2.18 mmol) and methanol/tetrahydrofuran (12.5 mL, 1:1.5) was added 2N sodium hydroxide (5.4 mL, 10.89 mmol) at room temperature. The yellow solution was stirred at that temperature for seventy minutes before it was concentrated. Water (20 mL) was added and the mixture was adjusted to pH=2 with 1N HCl (13 mL). The mixture was then extracted with dichloromethane and ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, concentrated in vacuo to give the title compound as a yellow solid (647 mg): MS: (+) m/z 320.80 (M+1).

後処理

  1. concentrationwas concentrated
  2. additionWater (20 mL) was added
  3. extractionThe mixture was then extracted with dichloromethane and ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-8114a5f0191d4d979dca22b5211cd701
出典データセット
uspto-grants-2015_11
特許番号
US09174976B2

反応ノート

読み込み中…