Triethylamine → 2-Amino-6-chloropyridine-3-carboxamide

HRID 2201554Notes

Reaction equation

HRID 2201554 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C1C=CC2N(O)N=[N:18]C=2C=1.CCN=C=NCCCN(C)C.C(N(CC)CC)C.[NH4+].[Cl-]>CN(C=O)C>[NH2:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:18])=[O:5]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 122639922-Amino-6-chloronicotinic acid

Product 1

HCID 226076432-Amino-6-chloropyridine-3-carboxamideYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-6-chloronicotinic acid (1.0 g, 5.79 mmol), HOBT (932 mg, 6.95 mmol) and EDCI (2.22 g, 11.6 mmol) in 15 mL of DMF was added triethylamine (5.86 g, 57.9 mmol) and NH4Cl (1.55 g, 28.9 mmol). Then the mixture was stirred at room temperature for 16 h. The solution was concentrated in vacuo to remove DMF and the residue was suspended in saturated NaHCO3 Finally the 2-amino-6-chloronicotinamide (800 mg, yield: 81%) was obtained by filtration without further purification. 1H-NMR (DMSO-d6, 400 MHz) δ 7.95 (d, J=8.4 Hz, 1H), 7.62 (s, 2H), 7.39 (s, 2H), 6.59 (d, J=8.4 Hz, 1H). MS (M+H)+: 172/174.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customto remove DMF

Sources & evidence

ORD record
ord-caab586f5e46466388e8f3efb3af5ecc
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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