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2-(Dimethylamino)ethanol → 2-(Dimethylamino)ethyl 4,6-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxylate

HRID 2379586
ノート
印刷プレビュー

反応式

HRID 2379586 の反応式
[O:1]=[C:2]1[N:7]2[CH2:8][C:9]3[C:14]([C:6]2=[C:5]([C:15]([OH:17])=[O:16])[CH:4]=[C:3]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3.[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27]O.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>O1CCOCC1.CN(C)C1C=CN=CC=1>[O:1]=[C:2]1[N:7]2[CH2:8][C:9]3[C:14]([C:6]2=[C:5]([C:15]([O:17][CH2:27][CH2:26][N:25]([CH3:29])[CH3:24])=[O:16])[CH:4]=[C:3]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 79022-(Dimethylamino)ethanolHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate2 回HCID 156408234,6-Dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxylic acid

生成物 1

HCID 189570492-(Dimethylamino)ethyl 4,6-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxylate

試薬・触媒・溶媒 2

HCID 14284
4-(Dimethylamino)pyridine
触媒
HCID 312751,4-Dioxane溶媒

実験手順

A suspension of 9.0 g of 4,6-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxylic acid in 240 ml of dioxane was treated in succession with 6.7 ml of 2-(dimethylamino)ethanol, 15.7 g of 1H-1-benzotriazolyloxy-tris(dimethylamino)phosphonium hexafluorophosphate and 263 mg of 4-dimethylaminopyridine, whereupon the mixture was heated to boiling under reflux for 80 minutes under argon, treated with 1.58 g of 1-benzotriazolyloxy-tris(dimethylamino)phosphonium hexafluorophosphate and heated for a further 1 hour. The mixture was then left to cool and the separated crystals were filtered off under suction. After stirring with 890 ml of methylene chloride, 475 ml of water and 70 ml of saturated sodium hydrogen carbonate solution for 90 minutes the organic phase was separated and evaporated. The residue was dissolved in 100 ml of methanol, whereupon the solution was acidified with ethereal hydrochloric acid, filtered and the product was precipitated by cooling in an ice bath. There was obtained 2.9 g of 2-(dimethylamino)ethyl 4,6dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxylate as yellowish crystals with a m.p. of 225°-228°.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 80 minutes under argon
  3. temperatureheated for a further 1 hour
  4. waitThe mixture was then left
  5. temperatureto cool
  6. filtrationthe separated crystals were filtered off under suction
  7. customwas separated
  8. customevaporated
  9. dissolutionThe residue was dissolved in 100 ml of methanol, whereupon the solution
  10. filtrationfiltered
  11. customthe product was precipitated
  12. temperatureby cooling in an ice bath

出典と根拠

ORDレコード
ord-558a931d070447d5b4537c4a67301c11
出典データセット
uspto-grants-1994_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05362738

反応ノート

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