Sodium hydride → (E)-3-[5-(4-Fluorophenyl)-1,2-dihydro-7-isopropyl-2-oxo1, 8-naphthyridin-6-yl]-prop-2-enal

HRID 1087048ノート

反応式

HRID 1087048 の反応式
C1(NC=CP(=O)(OCC)[O:11][CH2:12][CH3:13])CCCCC1.[H-].[Na+].[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[C:36]([CH:37]=O)=[C:35]([CH:39]([CH3:41])[CH3:40])[N:34]=[C:33]3[C:28]=2[CH:29]=[CH:30][C:31](=[O:42])[NH:32]3)=[CH:23][CH:22]=1.O.O.C(O)(=O)C(O)=O>O1CCCC1.O.C1(C)C=CC=CC=1>[F:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[C:36](/[CH:37]=[CH:13]/[CH:12]=[O:11])=[C:35]([CH:39]([CH3:40])[CH3:41])[N:34]=[C:33]3[C:28]=2[CH:29]=[CH:30][C:31](=[O:42])[NH:32]3)=[CH:25][CH:26]=1

参加物

8

反応物 4

HCID 24758Sodium hydrideHCID 61373Oxalic acid dihydrateHCID 89268Diethyl [2-(cyclohexylamino)vinyl]phosphonateHCID 148505585-(4-Fluorophenyl)-6-formyl-1,2-dihydro-7-isopropyl-2-oxo-1,8-naphthyridine

生成物 1

HCID 14850559(E)-3-[5-(4-Fluorophenyl)-1,2-dihydro-7-isopropyl-2-oxo1, 8-naphthyridin-6-yl]-prop-2-enal

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

A solution of 13.1 g (50 mmol) of diethyl 2-(cyclohexylamino)-vinyl-phosphonate in 80 ml of tetrahydrofuran is added dropwise at 0° C. under argon to a suspension of 3.0 g (100 mmol) of 80% strength sodium hydride in 80 ml of anhydrous tetrahydrofuran and the mixture is stirred at this temperature for 30 min. A solution of 13.0 g (42 mmol) of the compound from Example 4 in 80 ml of tetrahydrofuran is then added dropwise at 0° C.-5° C. and the mixture is then heated under reflux for 1 h. 200 ml of water are added cautiously and the mixture is extracted three times with ethyl acetate. After concentrating the organic phases, the residue is heated under reflux for 2 h with a mixture of 500 ml of toluene, 500 ml of water and 27.5 g (218 mmol) of oxalic acid dihydrate. The toluene phase is concentrated and the residue is treated with ethyl acetate. 11.35 g (80% of theory) of colorless crystals of m.p. 261° C. are obtained.

後処理

  1. temperaturethe mixture is then heated
  2. temperatureunder reflux for 1 h
  3. extractionthe mixture is extracted three times with ethyl acetate
  4. concentrationAfter concentrating the organic phases
  5. temperaturethe residue is heated
  6. concentrationThe toluene phase is concentrated
  7. additionthe residue is treated with ethyl acetate
  8. custom11.35 g (80% of theory) of colorless crystals of m.p. 261° C. are obtained

出典と根拠

ORDレコード
ord-d28aec44ba5846a2a9d14544a492910a
出典データセット
uspto-grants-1991_07
特許番号
US05034399

反応ノート

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