Hydrochloric Acid → HCID 19748915、化合物

HRID 1031927ノート

反応式

HRID 1031927 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][N:14]=1.C(N(CC)[C:26](=[O:34])[C:27]1[CH:32]=[CH:31][CH:30]=[N:29][C:28]=1[CH3:33])C.[ClH:37].[NH4+].[OH-]>O1CCCC1.O>[ClH:37].[CH:21]1[C:22]2[CH:13]3[N:14]([C:26](=[O:34])[C:27]4[CH:32]=[CH:31][CH:30]=[N:29][C:28]=4[CH2:33]3)[CH2:15][CH2:16][C:17]=2[CH:18]=[CH:19][CH:20]=1

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 14923Ammonium HydroxideHCID 767053,4-DihydroisoquinolineHCID 14307657N,N-Diethyl-2-methylpyridine-3-carboxamideHCID 178418339Butyllithium

生成物 1

HCID 19748915HCID 19748915、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-20 °C

実験手順

Diisopropylamine (28 ml) and 150 ml of tetrahydrofuran were cooled to -65° C. and 125 mL of 1.6M n-butyllithium was added. To the resulting solution was added a solution of 16.2 g of 3,4-dihydroisoquinoline and 38.4 g of 2-methylnicotinic acid diethylamide in tetrahydrofuran. The mixture was allowed to warm to -20° C. and 600 ml of 3N hydrochloric acid was then added followed by 200 ml of water. The mixture was basified with NH4OH and extracted twice with ether. The ether extracts were combined, dried over anhydrous magnesium sulfate and evaporated to a residue, which was dissolved in methanol and acidified with anhydrous HCl in ether. Acetone (50 ml) was added and the mixture was allowed to stand overnight. The crystalline product was collected by filtration, yielding 34 g of (±) 5,6,13,13a-tetrahydroisoquino[2,1-g][1,6]naphthyridine-8-one hydrochloride, m.p. 220°-222° C.

後処理

  1. extractionextracted twice with ether
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated to a residue, which
  4. dissolutionwas dissolved in methanol
  5. additionAcetone (50 ml) was added
  6. filtrationThe crystalline product was collected by filtration

出典と根拠

ORDレコード
ord-d24b765160214976ba4d72cbd01c52d0
出典データセット
uspto-grants-1990_09
特許番号
US04956365

反応ノート

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