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

HRID 1928861Notes

Reaction equation

HRID 1928861 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.[CH3:15][O:16][C:17]1[C:22]2[CH:23]([NH2:26])[CH2:24][O:25][C:21]=2[CH:20]=[CH:19][CH:18]=1.C(N(C(C)C)C(C)C)C>CN1CCCC1=O>[CH3:15][O:16][C:17]1[C:22]2[CH:23]([NH:26][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)[CH2:24][O:25][C:21]=2[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 109217232-Chloro-6-nitroquinolineHCID 672125224-Methoxy-2,3-dihydrobenzofuran-3-amine

Product 1

HCID 68633781N-(2,3-dihydro-4-methoxy-3-benzofuranyl)-6-nitro-2-quinolinamineYield 65.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-chloro-6-nitro-quinoline (3.8 g, 18.2 mmol) in 1-methyl-2-pyrrolidone (5 mL) with the above described rac-4-methoxy-2,3-dihydro-benzofuran-3-ylamine (3.61 g, 21.9 mmol) and N-ethyldiisopropylamine (4.68 mL, 27.3 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 (4.0 g, 65%); MS: m/e=336.3 (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-03e4d644199f4ae6b17ed03001c1d29a
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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