Butylethylamine → HCID 10516302, compound

HRID 1872065Notes

Reaction equation

HRID 1872065 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[CH:5]=[C:4]([CH3:12])[N:3]=1.[CH2:13]([NH:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH3:14].C(N(CC)C(C)C)(C)C>>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([N:15]([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:13][CH3:14])[CH:5]=[C:4]([CH3:12])[N:3]=1

Participants

4

Reactant 3

HCID 25914ButylethylamineHCID 81531DiisopropylethylamineHCID 27848192,4-Dichloro-6-methyl-3-nitropyridine

Product 1

HCID 10516302HCID 10516302, compound

Procedure

2,4-Dichloro-6-methyl-3-nitropyridine (1 g, 4.83 mmol), N-ethylbutylamine (0.75 mL, 5.55 mmol), and N,N-diisopropylethylamine (1 mL, 6 mmol) were stirred at 25° C. for 24 h and at reflux for 5 h. Then the mixture was stripped in vacuo and the residue was partitioned between EtOAc (75 mL), and water (50 mL). The organic layer was washed with water (30 mL), brine (30 mL), dried (MgSO4) and stripped in vacuo. The residue was chromatographed on silica gel (10%) EtOAc/hexanes eluent) to give the two regiomers 270 mg and 840 mg. The major regioisomer was characterized as the 4-adduct by nOe NMR experiments. minor: NMR (CDCl3) 6.56 (s, 1H), 3.30-3.42 (m, 4H), 2.38 (s, 3H), 1.49-1.59 (m, 2H), 1.23-1.35 (m, 2H), 1.15 (t, 3H, J=7.3 Hz), 0.92 (t, 3H, J=7.0 Hz); major: NMR (CDCl3) 6.52 (s, 1H), 3.28 (q, 2H, J=7.0), 3.18 (dd, 2H, J1 =7.3 Hz, J2 =8.1 Hz), 2.44 (s, 3H), 1.49-1.60 (m, 2H), 1.24-1.37 (m, 2H), 1.17 (t, 3H, J=7.3 Hz), 0.94 (t 3H, J=7.3 Hz).

Workup

  1. temperatureat reflux for 5 h
  2. customthe residue was partitioned between EtOAc (75 mL), and water (50 mL)
  3. washThe organic layer was washed with water (30 mL), brine (30 mL)
  4. dry with materialdried (MgSO4)
  5. customThe residue was chromatographed on silica gel (10%) EtOAc/hexanes eluent)
  6. customto give the two regiomers 270 mg and 840 mg

Sources & evidence

ORD record
ord-8124bd5664474d8d9ab06e6f3444f5dd
Source dataset
uspto-grants-2000_08
Patent number
US06107301

Reaction notes

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