Diisopropylethylamine → Rac-(7-methoxy-indan-1-yl)-(6-nitro-quinolin-2-yl)-amine

HRID 1928858Notes

Reaction equation

HRID 1928858 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[CH:18]=[CH:19][CH:20]=[C:21]2[C:25]=1[CH:24]([NH2:26])[CH2:23][CH2:22]2.C(N(C(C)C)C(C)C)C>CN1CCCC1=O>[CH3:15][O:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:25]=1[CH:24]([NH:26][C:2]1[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=3)[N:3]=1)[CH2:23][CH2:22]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 109217232-Chloro-6-nitroquinolineHCID 186198817-Methoxy-2,3-dihydro-1H-inden-1-amine

Product 1

HCID 68632201Rac-(7-methoxy-indan-1-yl)-(6-nitro-quinolin-2-yl)-amineYield 80%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-chloro-6-nitro-quinoline (1.8 g, 8.62 mmol) in 1-methyl-2-pyrrolidone (5 mL) with the above described 7-methoxy-indan-1-ylamine (1.69 g, 10.35 mmol) and N-ethyldiisopropylamine (2.22 mL, 12.94 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 (2.3 g, 80%); 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-8da03591bf89413db035d426a08af6c3
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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