Dimethylformamide → Bis[2-(4-pyridyl)ethyl]amine

HRID 850468Notes

Reaction equation

HRID 850468 reaction equation
OC1[C:3]([N+:12]([O-])=O)=[C:4]([CH:7]=[CH:8][C:9]=1OC)C=O.OC1C=[C:18]([C:21]([N+:26]([O-])=O)=CC=1OC)C=O.[C:29](=O)([O-])[O-].[K+].[K+].BrC[CH2:37][CH2:38][CH2:39][CH3:40].C[N:42]([CH:44]=O)[CH3:43]>CCCCCC.C(OCC)(=O)C.O>[N:42]1[CH:44]=[CH:40][C:39]([CH2:38][CH2:37][NH:26][CH2:21][CH2:18][C:7]2[CH:4]=[CH:3][N:12]=[CH:9][CH:8]=2)=[CH:29][CH:43]=1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 2211913-Hydroxy-4-methoxy-2-nitrobenzaldehydeHCID 2852945-Hydroxy-4-methoxy-2-nitrobenzaldehyde

Product 1

HCID 416637Bis[2-(4-pyridyl)ethyl]amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-hydroxy4-methoxy-2-nitrobenzaldehyde and 3-hydroxy4-methoxy-6-nitrobenzaldehyde, and DMF (700 ml) were mixed, and potassium carbonate (136.7 mg, 989 mmol) and bromopentane (122.7 ml, 989 mmol) were successively added to this solution. The reaction mixture was stirred at 100° C. for 4 hours and fltered. Water (600 ml) and hexane-ethyl acetate (1:1, 600 ml) were added to the filtrate for separation. The aqueous layer was extracted with hexane-ethyl acetate (1:1, 600 ml). The organic layers were combined, and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was evaporated. The precipitated crystals were collected by filtration to give 4-methoxy-6-nitro-3-pentyloxybenzaldehyde (2)) (90.1 g, 44%) as yellow crystals. The filtrate after filtration of said crystals was further evaporated to give 4-methoxy-2-nitro-3-pentyloxybenzaldehyde (1) (117 g, 58%) as a red oil.

Workup

  1. additionwere mixed
  2. extractionThe aqueous layer was extracted with hexane-ethyl acetate (1:1, 600 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe drying agent was filtered off
  5. customthe filtrate was evaporated
  6. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-469c72f457f440e9a1fdabf715508a43
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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