Hydrochloric Acid → HCID 19748915, 화합물

HRID 484006노트

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HRID 484006 반응식
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

참가 물질

9

반응물 6

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

생성물 1

HCID 19748915HCID 19748915, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

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온도
-20 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c62d972f0706462cb94b99349bdf2f64
출처 데이터셋
uspto-grants-1993_07
특허 번호
US05229387

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