2-Chloroaniline → HCID 67958530, compound

HRID 509579Notes

Reaction equation

HRID 509579 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C[Al](C)C.[CH2:13]([O:15][C:16]1[CH:17]=[CH:18][C:19]([C:22](OCC)=[O:23])=[N:20][CH:21]=1)[CH3:14]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:22]([C:19]1[CH:18]=[CH:17][C:16]([O:15][CH2:13][CH3:14])=[CH:21][N:20]=1)=[O:23]

Participants

5

Reactant 3

HCID 72402-ChloroanilineHCID 16682925TrimethylaluminumHCID 67958698Ethyl 5-ethoxypicolinate

Product 1

HCID 67958530HCID 67958530, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of o-chloroaniline (0.68 g, 5.3 mmol) in 20 mL of PhMe was added 3 mL of AlMe3. The mixture was stirred at ambient temperature for 0.5 h and added into a solution of ethyl 5-ethoxypyridine-2-carboxylate 3 (0.26 g, 1.33 mmol) in 10 mL of PhMe. The mixture was stirred at ambient temperature for 15 h and quenched with 20 mL of 1N HCl. The mixture was extracted with ethyl acetate. The organic layer was separated and concentrated. The residue was purified by column (2:1 of hexane/ethyl acetate) to give N-(2-chlorophenyl)-5-ethoxypyridine-2-carboxamide 4 as a solid. Yield: 310 mg, 96%.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 15 h
  2. customquenched with 20 mL of 1N HCl
  3. extractionThe mixture was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. concentrationconcentrated
  6. customThe residue was purified by column (2:1 of hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2b13776d4ebb4471bdbad8c35aa45cd3
Source dataset
uspto-grants-2015_08
Patent number
US09096587B2

Reaction notes

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