Nitrogen → HCID 13802441, compound

HRID 1799794Notes

Reaction equation

HRID 1799794 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].[NH:13]1[CH2:17][CH:16]=[CH:15][CH2:14]1.N#N>C(Cl)Cl>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[N:13]1[CH2:17][CH:16]=[CH:15][CH2:14]1

Participants

5

Reactant 3

HCID 947NitrogenHCID 660593-PyrrolineHCID 705192-Chloro-5-nitroanisole

Product 1

HCID 13802441HCID 13802441, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-chloro-2-methoxy-4-nitrobenzene (2.71 g, 14.47 mmol) and 2,5-dihydro-1H-pyrrole (2.0 g, 28.9 mmol) was stirred at 100° C. under a stream of N2 for 10 h. The reaction was cooled to RT to give a brown solid which was dissolved in CH2Cl2 (200 mL), washed with 100 mL of 1 N NaOH solution and brine, dried over MgSO4, and concentrated. The resulting brown oil was purified by flash chromatography (silica gel, Hexanes:EtOAc, 100:0 to 80:20) to afford the title compound (2.67 g, 84% yield) as a orange solid: 1H NMR (500 MHz, CDCl3) δ 7.84 (dd, J=8.80, 2.50 Hz, 1H), 7.65 (d, J=2.50 Hz, 1H), 6.39 (d, J=8.80 Hz, 1H), 5.89 (s, 2H), 4.46 (s, 4H), 3.83 (s, 3H). HPLC retention time: 3.315 min; LCMS (ES): m/z 221 [M+H]+.

Workup

  1. customto give a brown solid which
  2. washwashed with 100 mL of 1 N NaOH solution and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe resulting brown oil was purified by flash chromatography (silica gel, Hexanes:EtOAc, 100:0 to 80:20)

Sources & evidence

ORD record
ord-322868491f6542f9a4cb74dceaaf8b2e
Source dataset
uspto-grants-2013_01
Patent number
US08344160B2

Reaction notes

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