Triethylamine → HCID 86702329, compound

HRID 2279073Notes

Reaction equation

HRID 2279073 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[C:15]([NH2:16])=[CH:14][CH:13]=[CH:12][N:11]=1.Cl[C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[C:20]([Cl:27])[N:19]=1>C(#N)C>[Cl:27][C:20]1[N:19]=[C:18]([NH:16][C:15]2[C:10]([O:9][CH3:8])=[N:11][CH:12]=[CH:13][CH:14]=2)[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 852392,6-Dichloro-3-nitropyridineHCID 27374883-Amino-2-methoxypyridine

Product 1

HCID 86702329HCID 86702329, compoundYield 14.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triethylamine (6.5 mL, 46.6 mmol) was added to a solution of 2-methoxypyridin-3-amine (1.0 g, 8.1 mmol) and 2,6-dichloro-3-nitropyridine (1.62 g, 8.4 mmol) in acetonitrile (30 mL) and the resulting mixture was stirred at ambient temperature for 5 days and then at 50° C. for 24 h. The precipitate formed was filtered, washed with acetonitrile and dried in vacuo. The solid was then treated with tetrahydrofuran, filtered, washed with more tetrahydrofuran and the combined filtrate and washings were concentrated to dryness under reduced pressure to yield the title compound (0.32 g, 11%) as an orange solid.

Workup

  1. waitat 50° C. for 24 h
  2. customThe precipitate formed
  3. filtrationwas filtered
  4. washwashed with acetonitrile
  5. customdried in vacuo
  6. additionThe solid was then treated with tetrahydrofuran
  7. filtrationfiltered
  8. washwashed with more tetrahydrofuran
  9. concentrationthe combined filtrate and washings were concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-00e241dfbea9447685967603bec19e13
Source dataset
uspto-grants-2015_09
Patent number
US09133200B2

Reaction notes

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