Diisopropylethylamine → HCID 68632710, compound

HRID 1928865Notes

Reaction equation

HRID 1928865 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][CH2:17][CH2:18][O:19][C:20]1[C:25]2[CH:26]([NH2:29])[CH2:27][O:28][C:24]=2[CH:23]=[CH:22][CH:21]=1.C(N(C(C)C)C(C)C)C>CN1CCCC1=O>[CH3:15][O:16][CH2:17][CH2:18][O:19][C:20]1[C:25]2[CH:26]([NH:29][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)[CH2:27][O:28][C:24]=2[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 109217232-Chloro-6-nitroquinolineHCID 68631193HCID 68631193, compound

Product 1

HCID 68632710HCID 68632710, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-chloro-6-nitro-quinoline (1.04 g, 5.0 mmol) in 1-methyl-2-pyrrolidone (10 mL) with the above described rac-4-(2-methoxy-ethoxy)-2,3-dihydro-benzofuran-3-ylamine (1.14 g, 5.5 mmol) and N-ethyldiisopropylamine (1.27 mL, 7.5 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 an orange solid (1.24 g, 65%); MS: m/e=382.3 (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-401ebe073b7042678b22f252e2bae668
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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