Triethylamine → Ethyl (5-Iodo-3-nitropyridin-2-yl)glycinate

HRID 659315Notes

Reaction equation

HRID 659315 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([I:11])=[CH:4][N:3]=1.Cl.[CH2:13]([O:15][C:16](=[O:19])[CH2:17][NH2:18])[CH3:14].C(N(CC)CC)C>C(O)C>[CH2:13]([O:15][C:16](=[O:19])[CH2:17][NH:18][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([I:11])=[CH:4][N:3]=1)[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15142942-Chloro-5-iodo-3-nitropyridineHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 57885827Ethyl (5-Iodo-3-nitropyridin-2-yl)glycinateYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-5-iodo-3-nitro-pyridine (13 g) was dissolved in ethanol. Glycine ethyl ester HCl was added (5.0 eq) followed by triethylamine (5.0 eq). The reaction mixture was heated to 80° C. for four (4) hours. The reaction mixture was concentrated to dryness and triturated with H2O to give the title compound as a white solid (82-94% yield). M.p. 200° C. (dec), LCMS: m/z=352.08 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 1.30 (t, J=7.1 Hz, 3H), 4.25 (q, J=7.1 Hz, 2H), 4.33 (d, J=5.6 Hz, 2H), 8.44 (bs, 1H), 8.52 (d, J=2.0 Hz, 1H), 8.69 (d, J=2.0 Hz, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customtriturated with H2O

Sources & evidence

ORD record
ord-32fd94e3a07d45e781eed6889e8f8e51
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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