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CAS No. : | 2696-85-7 | MDL No. : | MFCD00130033 |
Formula : | C10H15N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HDVUPIFFKAHPJY-UHFFFAOYSA-N |
M.W : | 149.23 | Pubchem ID : | 75909 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
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With hydrogenchloride; zinc | ||
With hydrogenchloride; tin | ||
With acetic acid; platinum Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
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0.90 g (79%) | In hexane; toluene | 6 4-Amino-8-butylquinoline-3-(N-propyl)carboxamide (Formula I, Ra=butyl, Rb=propyl, Rc=Rd=hydrogen) Example 6 4-Amino-8-butylquinoline-3-(N-propyl)carboxamide (Formula I, Ra=butyl, Rb=propyl, Rc=Rd=hydrogen) The processes described in Examples 1b-1e were repeated using 2-butylaniline (2.26 g) in Example 1b instead of 2-ethylaniline. A quinoline ester of formula IIa (Ra=butyl, Rd=H, A1=-COOCH2CH3) was obtained. Then to a 0°C suspension of propylamine hydrochloride (0.96 g) in toluene was added dropwise a 2.3 M solution of trimethylaluminum (4.35 ml) in hexane. Following the addition the mixture was warmed to ambient temperature and stirred for 1 hr during which time the suspended amine hydrochloride was consumed. The resulting solution was cooled to 0° and the quinoline ester (1.09 g) was added quickly under a blanket of nitrogen. The mixture was heated to 100° and stirred for 2 hr. After cooling, the mixture was carefully quenched with aqueous hydrochloric acid and the mixture extracted with both ethyl acetate and CH2Cl2. The combined extracts were dried (MgSO4) and concentrated to leave a crude solid. Purification by column chromatography over silica gel eluding with ethyl acetate/hexane (2:3) afforded a white solid. Recrystallization from CH2Cl22/hexane gave 0.90 g (79%) of the title compound, m.p. 128-129°. |
0.90 g (79%) | In hexane; toluene | 6 (Formula I, Ra=butyl, Rb=propyl, Rc=Rd=hydrogen) EXAMPLE 6 4-Amino-8-butylquinoline-3-(N-propyl)carboxamide (Formula I, Ra=butyl, Rb=propyl, Rc=Rd=hydrogen) The processes described in Examples 1b-1e were repeated using 2-butylaniline (2.26 g) in Example 1b instead of 2-ethylaniline. A quinoline ester of formula IIa (Ra=butyl, Rd=H, A1 =--COOCH2 CH3) was obtained. Then to a 0° C. suspension of propylamine hydrochloride (0.96 g) in toluene was added dropwise a 2.3M solution of trimethylaluminum (4.35 ml) in hexane. Following the addition the mixture was warmed to ambient temperature and stirred for 1 hr during which time the suspended amine hydrochloride was consumed. The resulting solution was cooled to 0° and the quinoline ester (1.09 g) was added quickly under a blanket of nitrogen. The mixture was heated to 100° and stirred for 2 hr. After cooling, the mixture was carefully quenched with aqueous hydrochloric acid and the mixture extracted with both ethyl acetate and CH2 Cl2. The combined extracts were dried (MgSO4) and concentrated to leave a crude solid. Purification by column chromatography over silica gel eluding with ethyl acetate/hexane (2:3) afforded a white solid. Recrystallization from CH2 Cl2 /hexane gave 0.90 g (79%) of the title compound, m.p. 128°-129°. Analysis calculated for C17 H23 N3 O: C, 71.55; H, 8.12; N, 14.72. Found: C, 71.23; H, 7.89; N, 14.69. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In toluene; for 3h;Reflux; | A solution of 2-butylbenzenamine (101?ml, 640.4?mmol) in toluene (100?ml) was added drop-wise to a mixture of 5-formylthiophene-2-carboxylic acid (108; 100?g, 640.4?mmol) in toluene (600?ml) and the resulting mixture heated to reflux for 3?h. After cooling to 90?°C, n-heptane (500?ml) was added and the resulting solution seeded with small crystals of the desired product at 68?°C. After cooling to room temperature, the precipitated solid was filtered and washed with n-heptane (1?L). The filter cake was dried in a vacuum to afford (E)-5-(((2-butylphenyl)imino)methyl)thiophene-2-carboxylic acid (110; 171.5?g, 93percent) as a pale yellow solid. 1H NMR (CDCl3, 400?MHz) delta: 0.93 (t, J?=?7.3?Hz, 3H), 1.33-1.42 (m, 2H), 1.58 (tt, J?=?8.6, 3.6?Hz, 2H), 2.80 (t, J?=?7.8?Hz, 2H), 6.99-7.02 (m, 1H), 7.18-7.27 (m, 3H), 7.47 (d, J?=?3.9?Hz, 1H), 7.90 (d, J?=?3.9?Hz, 1H), 8.53 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diphenyl hydrogen phosphate In dichloromethane at 20℃; for 2h; |