Chlorine → Ethyl 2-amino-5-chloro-6-[(2,2-dimethylpropanoyl)amino]nicotinate

HRID 965788Notes

Reaction equation

HRID 965788 reaction equation
[NH2:1][C:2]1[N:12]=[C:11]([NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[Cl:20]Cl>C(O)(=O)C>[NH2:1][C:2]1[N:12]=[C:11]([NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[C:10]([Cl:20])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 24526ChlorineHCID 12088088Ethyl 2-amino-6-[(2,2-dimethylpropanoyl)amino]nicotinate

Product 1

HCID 12088089Ethyl 2-amino-5-chloro-6-[(2,2-dimethylpropanoyl)amino]nicotinateYield 76%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of ethyl 2-amino-6-[(2,2-dimethylpropanoyl)amino]nicotinate (Example 1, METHOD A, Step 1, 805 mg, 3.03 mmol) in acetic acid (15 ml) was added a solution of chlorine in acetic acid (0.89 M, 8.5 mL, 7.6 mmol), and the mixture was stirred at room temperature for 15 min. The solvent was removed in vacuo. The obtained residue was taken up in ethyl acetate (150 mL) and washed with saturated sodium bicarbonate, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on a column of silica gel eluting with ethyl acetate/pentane (1:2) to give 685 mg (76%) of the title compound as a white crystal.

Workup

  1. customThe solvent was removed in vacuo
  2. washwashed with saturated sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on a column of silica gel eluting with ethyl acetate/pentane (1:2)

Sources & evidence

ORD record
ord-21bf6fda5bb14df09fec0d827b697347
Source dataset
uspto-grants-2005_10
Patent number
US06951867B2

Reaction notes

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