Aniline → HCID 3785006, compound

HRID 333544Notes

Reaction equation

HRID 333544 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18]([Cl:25])[N:17]=1>C(O)C>[Cl:25][C:18]1[N:17]=[C:16]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 3785006HCID 3785006, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of aniline (7.24 g, 78 mmol), triethylamine (13 mL, 93 mmol), and 2,6-dichloro-3-nitropyridine (15 g, 78 mmol) was stirred overnight in 500 mL ethanol at room temperature under nitrogen. The solid that formed was filtered off, washed with water and ethanol, and dried. The solid was purified by column chromatography eluting with 20% ethyl acetate/hexane (8.62 g, 44%).

Workup

  1. customThe solid that formed
  2. filtrationwas filtered off
  3. washwashed with water and ethanol
  4. customdried
  5. customThe solid was purified by column chromatography
  6. washeluting with 20% ethyl acetate/hexane (8.62 g, 44%)

Sources & evidence

ORD record
ord-62331cdeb83b4336af578d635869f59e
Source dataset
uspto-grants-2014_11
Patent number
US08883322B2

Reaction notes

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