Cyclopropylamine → 3-bromo-N-cyclopropyl-5-nitropyridin-4-amine

HRID 1394195Notes

Reaction equation

HRID 1394195 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1Cl.[CH:12]1([NH2:15])[CH2:14][CH2:13]1>ClCCl>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[NH:15][CH:12]1[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 125100523-Bromo-4-chloro-5-nitropyridine

Product 1

HCID 249036703-bromo-N-cyclopropyl-5-nitropyridin-4-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Step 2 (8.01 g, ca. 30 mmol) in dichloromethane (100 ml) at 0° C. was added cyclopropylamine (4.16 ml, 60 mmol) drop-wise. The resulting mixture was stirred overnight at room temperature, then concentrated under vacuum to a residue and re-dissolved in ethyl acetate, basifying with sodium bicarbonate. The organic phase was washed with water three times, followed by twice with brine before concentrating under vacuum to a crude solid. This oil was purified by column chromatography eluting with a gradient of 50% DCM/hexane to DCM affording product as a yellow solid, 6.22 g (80%); MS (ES+) m/e 258/260 [M+H]+.

Workup

  1. concentrationconcentrated under vacuum to a residue
  2. dissolutionre-dissolved in ethyl acetate
  3. washThe organic phase was washed with water three times
  4. concentrationbefore concentrating under vacuum to a crude solid
  5. customThis oil was purified by column chromatography
  6. washeluting with a gradient of 50% DCM/hexane to DCM affording product as a yellow solid, 6.22 g (80%)

Sources & evidence

ORD record
ord-195b510ac9e9405e8320c57d0bf26789
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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