Methanol → N-butyl-8-nitro-2-quinoline amine

HRID 2188609Notes

Reaction equation

HRID 2188609 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([N+:12]([O-:14])=[O:13])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.CO.C(OCC)C.[CH2:22]([NH2:26])[CH2:23][CH2:24][CH3:25]>>[CH2:22]([NH:26][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([N+:12]([O-:14])=[O:13])[CH:6]=[CH:7][CH:8]=2)[N:3]=1)[CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 8007ButylamineHCID 3194532-Chloro-8-nitroquinoline

Product 1

HCID 67057974N-butyl-8-nitro-2-quinoline amineYield 90%

Conditions

Temperature
78 °C

Procedure

2-chloro-8-nitroquinoline (0.20 g; 0.96 mmol) is suspended in 9.5 ml of 1-butylamine and the medium is heated under reflux (78° C.) for 15 hours. The yellow solution obtained is subsequently concentrated under vacuum. The crude reaction product is taken up in a minimum volume of CH3OH and poured over 3 ml of diethyl ether. After centrifugation, butyl ammonium chloride crystals are removed and the supernatant is concentrated under reduced pressure to yield N-butyl-8-nitro-2-quinoline amine in the form of a yellow oil (0.21 g; 0.86 mmol, yield=90%). NMR-1H (250 MHz, CDCl3) δ, ppm: 7.83 (dd, 3J (H, H)=7.5 Hz, 4J (H, H)=1.5 Hz, 1H); 7.77 (d, 3J (H, H)=9.0 Hz, 1H); 7.69 (dd, 3J (H, H)=8.0 Hz, 4J (H, H)=1.5 Hz, 1H); 7.14 (m, 1H), 6.67 (d, 3J (H, H)=9.0 Hz, 1H); 5.07 (s large, 1H); 3.47 (m, 2H); 1.60 (m, 2H); 1.39 (m, 2H); 0.93 (t, 3J (H, H)=7.5 Hz, 3H). NMR-13C (63 MHz, CDCl3) δ, ppm: 157.8 (Cq); 145.6 (Cq); 140.2 (Cq); 136.7 (CH); 131.5 (CH); 124.7 (CH); 124.1 (CH); 119.7 (CH); 113.3 (Cq); 41.3 (CH2); 31.5 (CH2); 20.2 (CH2); 13.8 (CH3). MS (CID, NH3): m/z=246 (MH+). Analysis (%) for C13H15N3O2: calculated C, 63.66; H, 6.16; N, 17.13. found C, 63.33; H, 6.21; N, 16.64.

Workup

  1. temperaturethe medium is heated
  2. customThe yellow solution obtained
  3. concentrationis subsequently concentrated under vacuum
  4. customThe crude reaction product
  5. customAfter centrifugation, butyl ammonium chloride crystals are removed
  6. concentrationthe supernatant is concentrated under reduced pressure

Sources & evidence

ORD record
ord-f2df8247e8934b0bb4d78c5367ae626c
Source dataset
uspto-grants-2012_12
Patent number
US08324196B2

Reaction notes

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