Nitrogen → HCID 67287411, compound

HRID 218850Notes

Reaction equation

HRID 218850 reaction equation
[N+:1]([C:4]1(O)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]1[O:10]C)([O-:3])=[O:2].CN([CH:16]=[O:17])C.N#N.Br[CH:21]([CH3:23])[CH3:22]>>[CH:21]([O:10][C:5]1[C:6]([O:17][CH3:16])=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])([CH3:23])[CH3:22]

Participants

5

Reactant 4

HCID 947NitrogenHCID 6228DimethylformamideHCID 63582-BromopropaneHCID 67287285HCID 67287285, compound

Product 1

HCID 67287411HCID 67287411, compoundYield 98%

Conditions

Temperature
55 °C

Procedure

To a solution of 2-nitroguaiacol (Thompson, M. J.; Zeegerers, P. J. Tetrahedron, 1990, 46, 2661; 0.5062 g; 3 mmol) in anhydrous DMF (5 ml) K2CO3 (0.41 g; 3 mmol) was added and resulting mixture was stirred for 15 min under reduced pressure and saturated with N2. To it, 2-bromopropane (1 ml; 10.6 mmol) was added and the reaction flask was sealed with septum and stirred overnight at 55° C. After evaporation of DMF under reduced pressure the residue was partitioned between diethyl ether (20 ml) and water (10 ml). The organic phase was washed with 2% aq. KOH (5 ml), brine, dried over anhydrous MgSO4, filtered off and filtrate evaporated to dryness. The residue was dissolved in small volume of CH2Cl2 and filtered through short column with SiO2, which was eluded with fresh CH2Cl2. The combined filtrates were evaporated to dryness under reduced pressure to give 2-isopropoxy-3-methoxynitrobenzene (0.62 g; 98% yield) as creamy syrup. 1H-NMR (CDCl3) 1.26 (d, 6H, J=6.17 Hz); 3.87 (s, 3H); 4.61 (m, 1H, J=6.17 Hz); 7.06 (m, 2H); 7.26 (m, 1H). This was dissolved in ethanol (30 ml) and the resulting mixture was degassed under reduced pressure. To it 10% Pd on carbon (0.22 g) was added and the mixture was saturated with H2 and stirred for 5 h under the balloon pressure of H2. The catalyst was removed by filtration through Celite. The filtrate was evaporated to dryness to give the title compound (0.702 g; 92.5% yield) as colourless oil. 1H-NMR (CDCl3) 1.28 (d, 6H, J=6.19 Hz); 3.7 broad s, 2H); 3.79 (s, 3H); 4.45 (m, 1H, J=6.19 Hz); 6.2-6.78 (m, 2H); 6.8(m, 1H).

Workup

  1. customresulting mixture
  2. customthe reaction flask was sealed with septum
  3. customAfter evaporation of DMF under reduced pressure the residue
  4. customwas partitioned between diethyl ether (20 ml) and water (10 ml)
  5. washThe organic phase was washed with 2% aq. KOH (5 ml), brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered off
  8. customfiltrate evaporated to dryness
  9. dissolutionThe residue was dissolved in small volume of CH2Cl2
  10. filtrationfiltered through short column with SiO2, which
  11. customThe combined filtrates were evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-cdc571ed57ad42a988a43e75c06d8c98
Source dataset
uspto-grants-2012_06
Patent number
US08198466B2

Reaction notes

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