Isoamylamine → HCID 15657938, compound

HRID 601320Notes

Reaction equation

HRID 601320 reaction equation
Cl[C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:13]([NH2:18])[CH2:14][CH:15]([CH3:17])[CH3:16].C(N(CC)CC)C>C(OCC)(=O)C>[CH2:13]([NH:18][C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:14][CH:15]([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 7894IsoamylamineHCID 8471TriethylamineHCID 2796614Ethyl chloronicotinate

Product 1

HCID 15657938HCID 15657938, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of ethyl 2-chloronicotinate (3.71 g, 20 mmol), isoamylamine (3.03 mL, 26 mmol) and triethylamine (3.62 mL, 26 mmol) was heated in a sealed tube at 140° C. for 8 hours, cooled to 25C, diluted with ethyl acetate and the mixture washed with water. The organic layer was extracted with 1N aqueous hydrochloric acid. The acidic aqueous layer was adjusted to pH 8.0 with saturated sodium bicarbonate solution then extracted with ethyl acetate (2 portions). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound (3.58 g, 76%). MS (DCI/NH3) m/z 237 (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.93 (d, J=6.25 Hz, 6 H) 1.31 (t, J=6.99 Hz, 3 H) 1.47 (q, J=6.99 Hz, 2 H) 1.64 (m, 1 H) 3.47 (m, 2 H) 4.28 (q, J=6.99 Hz, 2 H) 6.59 (dd, J=7.72, 4.78 Hz, 1 H) 7.90 (t, J=5.15 Hz, 1 H) 8.07 (dd, J=7.91, 2.02 Hz, 1 H) 8.28 (dd, J=4.78, 1.84 Hz, 1 H).

Workup

  1. washthe mixture washed with water
  2. extractionThe organic layer was extracted with 1N aqueous hydrochloric acid
  3. extractionthen extracted with ethyl acetate (2 portions)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d7cf2d17c2df4775ba6930b42d9f3265
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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