Diisopropylethylamine → N-(2,3-dihydro-4-methoxy-3-benzofuranyl)-6-nitro-2-quinolinamine

HRID 1928868Notes

Reaction equation

HRID 1928868 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=2)[N:3]=1.[CH2:15]([O:17][C:18]1[C:23]2[CH:24]([NH2:27])[CH2:25][O:26][C:22]=2[CH:21]=[CH:20][CH:19]=1)C.C(N(C(C)C)C(C)C)C>CN1CCCC1=O>[CH3:15][O:17][C:18]1[C:23]2[CH:24]([NH:27][C:2]3[CH:11]=[CH:10][C:9]4[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=4)[N:3]=3)[CH2:25][O:26][C:22]=2[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 109217232-Chloro-6-nitroquinolineHCID 686326984-Ethoxy-2,3-dihydro-3-benzofuranamine

Product 1

HCID 68633781N-(2,3-dihydro-4-methoxy-3-benzofuranyl)-6-nitro-2-quinolinamineYield 18.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-chloro-6-nitro-quinoline (2.0 g, 9.6 mmol) in 1-methyl-2-pyrrolidone (5 mL) with the above described rac-4-ethoxy-2,3-dihydro-benzofuran-3-ylamine (3.78 g, ca. 10 mmol, max. 50% purity) and N-ethyldiisopropylamine (2.45 mL, 14.4 mmol) was stirred at 140° C. for 2 h. Cooled to 23° C., poured onto water and extracted twice with ethyl acetate, dried over Na2SO4 and evaporated totally to give a crude product which was purified by silica gel column chromatography with heptane/dichloromethane followed by trituration with diethyl ether to give the title compound as a yellow solid (0.60 g, 18%); MS: m/e=352.4 (M+H+).

Workup

  1. temperatureCooled to 23° C.
  2. additionpoured onto water
  3. extractionextracted twice with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. customevaporated totally
  6. customto give a crude product which
  7. customwas purified by silica gel column chromatography with heptane/dichloromethane

Sources & evidence

ORD record
ord-58c112d2614140c7b66aa56f90fe44f5
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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