Acetic Acid → 2-[3-[(6-Bromohexyl)oxy]propyl]-5-nitropyridine

HRID 1649790Notes

Reaction equation

HRID 1649790 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][C:10]#[C:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=1.N(C([O-])=O)=NC([O-])=O.[K+].[K+].C(O)(=O)C>N1C=CC=CC=1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6096233HCID 6096233, compoundHCID 198548002-[3-[(6-Bromohexyl)oxy]-1-propynyl]-5-nitropyridine

Product 1

HCID 198547802-[3-[(6-Bromohexyl)oxy]propyl]-5-nitropyridineYield 5.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2-[3-[(6-bromohexyl)oxy]-1-propynyl]-5-nitropyridine (5 g) and dipotassium azodicarboxylate (30 g) in pyridine (200 ml) was stirred at room temperature, and acetic acid (18 ml) added. The mixture was stirred overnight and evaporated in vacuo to give a residue oil which was partitioned between 8% sodium bicarbonate (20 ml) and ethyl acetate (20 ml). The organic phase was dried and concentrated to give an oil which was purified by FCC eluting with hexane-ether (1:2→methanol) to give the title compound as an orange oil (300 mg), t.l.c. (toluene:ethanol 0.88 ammonia 80:20:1) Rf 0.75.

Workup

  1. stirringThe mixture was stirred overnight
  2. customevaporated in vacuo
  3. customto give a residue oil which
  4. customwas partitioned between 8% sodium bicarbonate (20 ml) and ethyl acetate (20 ml)
  5. customThe organic phase was dried
  6. concentrationconcentrated
  7. customto give an oil which
  8. customwas purified by FCC
  9. washeluting with hexane-ether (1:2→methanol)

Sources & evidence

ORD record
ord-00ba743695cd4e1ca809c606f41aeee2
Source dataset
uspto-grants-1990_05
Patent number
US04921867

Reaction notes

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