Cyclopropanemethanamine → HCID 22181445, compound

HRID 1796496Notes

Reaction equation

HRID 1796496 reaction equation
[CH:1]1([CH2:4][NH2:5])[CH2:3][CH2:2]1.Cl[C:7]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][N:8]=1>CO>[CH:1]1([CH2:4][NH:5][C:7]2[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][N:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 75646CyclopropanemethanamineHCID 3464596-CHLORO-5-NITRONICOTINIC ACID

Product 1

HCID 22181445HCID 22181445, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cyclopropanemethylamine (1.70 g, 23.90 mmol) was added to a solution of 6-chloro-5-nitronicotinic acid (1.12 g, 5.53 mmol) in MeOH (25 mL) at room temperature. The reaction mixture was stirred at room temperature for 2 h and concentrated in vacuo. The residue was dissolved in H2O (20 mL), and the solution was acidified by adding 3N HCl until pH=3. The mixture was extracted with EtOAc and CH2Cl2 (2×100 mL) and the combined extracts were washed with brine, dried over Na2SO4, concentrated in vacuo to give a bright yellow solid (1.30 g) which was used in the following reaction without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in H2O (20 mL)
  3. additionby adding 3N HCl until pH=3
  4. extractionThe mixture was extracted with EtOAc and CH2Cl2 (2×100 mL)
  5. washthe combined extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe8ffb94ed4547029f620f170387e489
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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