1-Butanol → 7-methoxy-N-methyl-N-(4-nitrophenyl)-1,5-naphthyridin-4-amine

HRID 1042823ノート

反応式

HRID 1042823 の反応式
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.Cl[C:30]1[CH:31]=[CH:32][N:33]=[C:34]2[C:39]=1[N:38]=[CH:37][C:36]([O:40][CH3:41])=[CH:35]2.CCCCO>[OH-].[Na+]>[CH3:41][O:40][C:36]1[CH:35]=[C:34]2[C:39]([C:30]([N:2]([CH3:1])[C:3]3[CH:4]=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=3)=[CH:31][CH:32]=[N:33]2)=[N:38][CH:37]=1

参加物

6

反応物 4

HCID 2631-ButanolHCID 7483N-Methyl-4-nitroanilineHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 594273408-Chloro-3-methoxy-1,5-naphthyridine

生成物 1

HCID 673172097-methoxy-N-methyl-N-(4-nitrophenyl)-1,5-naphthyridin-4-amine

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

反応条件

温度
100 °C

実験手順

To a resealable pressure vessel was added n-methyl-4-nitroaniline (0.911 ml, 7.19 mmol), pyridinium p-toluenesulfonate (1.81 g, 7.19 mmol), 8-chloro-3-methoxy-1,5-naphthyridine (1.000 g, 5.14 mmol), and n-BuOH (15 mL). The vessel was sealed and heated to 100° C. After 4 h, the mixture was cooled to RT, diluted with 1 N NaOH, and extracted with EtOAc. The organic fraction was dried with Na2SO4, concentrated in vacuo, and purified by silica gel chromatography using 50-100% Hexanes:EtOAc to afford 7-methoxy-N-methyl-N-(4-nitrophenyl)-1,5-naphthyridin-4-amine as a yellow solid. [email protected] min.

後処理

  1. customThe vessel was sealed
  2. temperaturethe mixture was cooled to RT
  3. extractionextracted with EtOAc
  4. dry with materialThe organic fraction was dried with Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-149101b1757b4709901e026ab61efc22
出典データセット
uspto-grants-2013_10
特許番号
US08557816B2

反応ノート

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