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 1825771ノート

反応式

HRID 1825771 の反応式
[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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-480816443c7c47078005c563183e527e
出典データセット
uspto-grants-2006_05
特許番号
US07049315B2

反応ノート

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