Aluminium lithium hydride → 8,9-Dimethoxy-2,3-methylenedioxy-5-[2-(N,N-dimethylamino)-1-methylethyl]-5,6-dihydro-dibenzo[c,h]1,6-naphthyridine

HRID 1825771노트

반응식

HRID 1825771 반응식
[CH3:1][O:2][C:3]1[C:4]([O:31][CH3:32])=[CH:5][C:6]2[C:15]3[C:10](=[C:11]4[CH:19]=[C:18]5[O:20][CH2:21][O:22][C:17]5=[CH:16][C:12]4=[N:13][CH:14]=3)[N:9]([CH:23]([CH3:28])[CH2:24][N:25]([CH3:27])[CH3:26])[C:8](=O)[C:7]=2[CH:30]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][O:2][C:3]1[C:4]([O:31][CH3:32])=[CH:5][C:6]2[C:15]3[C:10](=[C:11]4[CH:19]=[C:18]5[O:20][CH2:21][O:22][C:17]5=[CH:16][C:12]4=[N:13][CH:14]=3)[N:9]([CH:23]([CH3:28])[CH2:24][N:25]([CH3:26])[CH3:27])[CH2:8][C:7]=2[CH:30]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 221394918,9-Dimethoxy-2,3-methylenedioxy-5-[2-(N,N-dimethylamino)-1-methylethyl]-5H-dibenzo [c,h]1,6-naphthyridin-6-one

생성물 1

HCID 221395208,9-Dimethoxy-2,3-methylenedioxy-5-[2-(N,N-dimethylamino)-1-methylethyl]-5,6-dihydro-dibenzo[c,h]1,6-naphthyridine수율 45.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The title compound was prepared as follows. 8,9-Dimethoxy-2,3-methylenedioxy-5-[2-(N,N-dimethylamino)-1-methylethyl]-5H-dibenzo[c,h]1,6-naphthyridin-6-one (80 mg, 0.18 mmol; Example 7) in THF (150 mL) was added to LiAlH4 (50 mg, 1.3 mmol), and the mixture was stirred under nitrogen at reflux for 4h. The reaction was quenched by the sequential addition of water (5 drops), 10% NaOH (5 drops), and water (5 drops). The mixture was filtered through Celite and evaporated, and the crude mixture was chromatographed on silica in 1.0% methanol in chloroform to give 35 mg of the reduced product, in 45.4% yield; mp 153-154° C.; 1H NMR (CDCl3) δ 1.16 (d, 3H, J=8), 2.38 (dd, 2H, J=12.2, 8.0), 3.68-3.80 (m, 1), 3.88 (s, 3H), 4.24 (s, 2H), 6.16 (s, 2H), 6.64 (s, 1H), 7.24 (s, 1H), 7.40 (s, 2H), 7.62 (s, 1H), 8.88 (s, 1H); 13C NMR (CDCl3) δ: 17.7, 45.6, 46.0, 56.2, 56.4, 57.8, 64.2, 100.1, 101.7, 105.8, 106.4, 108.5, 120.5, 120.6, 123.6, 126.9, 143.4, 146.6, 147.7, 148.9, 149.5, 149.6, 150.0; HRMS calcd for C24H27N3O4H 422.2002; found 422.2081.

후처리

  1. temperatureat reflux for 4h
  2. customThe reaction was quenched by the sequential addition of water (5 drops), 10% NaOH (5 drops), and water (5 drops)
  3. filtrationThe mixture was filtered through Celite
  4. customevaporated
  5. customthe crude mixture was chromatographed on silica in 1.0% methanol in chloroform

출처 및 근거

ORD 기록
ord-480816443c7c47078005c563183e527e
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07049315B2

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