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

HRID 1042823노트

반응식

HRID 1042823 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-149101b1757b4709901e026ab61efc22
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557816B2

반응 노트

불러오는 중…