Methyl 2-benzyl-9-bromo-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate → Methyl 5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate hydrobromide

HRID 521418

反応式

HRID 521418 の反応式
C([N:8]1[CH2:17][C:16]2[NH:15][C:14]3[C:18]([Br:26])=[CH:19][CH:20]=[C:21]([C:22]([O:24][CH3:25])=[O:23])[C:13]=3[C:12](=[O:27])[C:11]=2[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[BrH:26].[O:27]=[C:12]1[C:11]2[CH2:10][CH2:9][NH:8][CH2:17][C:16]=2[NH:15][C:14]2[CH:18]=[CH:19][CH:20]=[C:21]([C:22]([O:24][CH3:25])=[O:23])[C:13]1=2

参加物

5

反応物 2

HCID 89657401Methyl 2-benzyl-9-bromo-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 89657238Methyl 5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate hydrobromide収率 65.1%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

To a solution of methyl 2-benzyl-9-bromo-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate (6.6 g, 15.4 mmol) in MeOH (100 mL) was added Pd/C (3.0 g, 5%, 50% water), the mixture was stirred at atmosphere of hydrogen for about 6.0 h. Then the mixture was filtered, washed with MeOH (20 mL). The filtrate was concentrated and the residue was recrystallized with MeOH (2.5 mL) to afford the product (3.4 g, 65%) as a white solid. 1H NMR (DMSO-d6) δ 12.0 (s, 1H), 9.18 (s, 1H), 7.61-7.72 (m, 2H), 7.22-7.23 (m, 1H), 4.32 (s, 2H), 3.81 (s, 3H), 3.38-3.40 (m, 2H), and 2.66-2.67 (m, 2H).

後処理

  1. filtrationThen the mixture was filtered
  2. washwashed with MeOH (20 mL)
  3. concentrationThe filtrate was concentrated
  4. customthe residue was recrystallized with MeOH (2.5 mL)

出典と根拠

ORDレコード
ord-7021bedf28204cc9b63209ef73a65e68
出典データセット
uspto-grants-2016_05
特許番号
US09328111B2

関連ノート

読み込み中…