2-Chloroaniline → HCID 67958530, compound

HRID 1478104Notes

Reaction equation

HRID 1478104 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-9030c4beb75440eea619a6bd91dc7c4c
Source dataset
uspto-grants-2016_08
Patent number
US09403812B2

Reaction notes

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