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

HRID 1042823Notes

Reaction equation

HRID 1042823 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-149101b1757b4709901e026ab61efc22
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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