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2-Bromopropan-1-ol → Bromo-3-isopropyl-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid ethyl ester

HRID 1765354
ノート
印刷プレビュー

反応式

HRID 1765354 の反応式
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12]([Br:16])=[N:11][NH:10][C:9]2=[O:17])=[O:5])[CH3:2].[H-].[Na+].Br[CH:21]([CH3:24])[CH2:22]O>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12]([Br:16])=[N:11][N:10]([CH:21]([CH3:24])[CH3:22])[C:9]2=[O:17])=[O:5])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 117132-Bromopropan-1-olHCID 24758Sodium hydrideHCID 57856207Bromo-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid ethyl ester

生成物 1

HCID 68898772Bromo-3-isopropyl-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid ethyl ester収率 34%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

Bromo-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid ethyl ester (6 g, 0.02 mol) was dissolved in dimethylformamide (DMF) (60 ml). To this was added NaH (60%, 0.97 g, 0.024 mol) as a DMF suspension (5 ml). The mixture was stirred at room temperature for 30 minutes then 2-bromo-propanol (3.7 g, 0.03 mol) was added in one portion as a solution in DMF (5 ml). The reaction mixture was stirred for 48 hours whereupon LC-MS showed complete consumption of starting material. The DMF was removed under vacuum and the resulting residue was partitioned between DCM (100 ml) and water (100 ml), the organic layer was dried (MgSO4), filtered and concentrated under vacuum. The resulting yellow oil was recrystallised from methanol to give the title compound (2.3 g, 34% yield) as a white solid. MS (ESI+)=(M+H)+ 339 & 341

後処理

  1. stirringThe reaction mixture was stirred for 48 hours whereupon LC-MS
  2. customconsumption of starting material
  3. customThe DMF was removed under vacuum
  4. customthe resulting residue was partitioned between DCM (100 ml) and water (100 ml)
  5. dry with materialthe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe resulting yellow oil was recrystallised from methanol

出典と根拠

ORDレコード
ord-027f3739a9e9442ebf1e033f9635527c
出典データセット
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07226923B2

反応ノート

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