3-Methoxypropylamine → HCID 59631510, compound

HRID 1431350Notes

Reaction equation

HRID 1431350 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](Cl)=[N:6][CH:7]=1.[CH3:12][O:13][CH2:14][CH2:15][CH2:16][NH2:17]>CS(C)=O.O>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([NH:17][CH2:16][CH2:15][CH2:14][O:13][CH3:12])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 16723-MethoxypropylamineHCID 70194125-Bromo-2-chloro-3-nitropyridine

Product 1

HCID 59631510HCID 59631510, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a 100 mL round bottom flask containing 5-bromo-2-chloro-3-nitropyridine (5.12 g, 21.6 mmol) in DMSO (20.5 mL) was added 3-methoxypropylamine (4.40 mL, 43.1 mmol) dropwise. The reaction was heated to 60° C. and monitored with TLC and LC-MS. After 2.5 h, LC-MS showed that the reaction was complete. The mixture was cooled to rt then diluted with water. After extracting three times with EtOAc, the organic layers were combined then washed with brine and dried over anhydrous magnesium sulfate. After filtration, the mixture was concentrated in vacuo to give a light yellow brown solid as 5-bromo-N-(3-methoxypropyl)-3-nitropyridin-2-amine. 1H NMR (400 MHz, CDCl3) δ ppm 8.62 (1H, br. s.), 8.54 (1H, d, J=2.3 Hz), 8.43 (1H, d, J=2.3 Hz), 3.69-3.78 (2H, m), 3.56 (2H, t, J=5.7 Hz), 3.40 (3H, s), 1.96 (2H, dt, J=12.2, 6.2 Hz).

Workup

  1. temperatureThe mixture was cooled to rt
  2. extractionAfter extracting three times with EtOAc
  3. washthe organic layers were combined then washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-8eff9fcbaee941aeadae29091a0be71b
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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