Benzoyl chloride → HCID 14390484, compound

HRID 2072910Notes

Reaction equation

HRID 2072910 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][NH:6][C:7]1[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[CH:9][N:8]=1)[CH3:2].C(N(CC)CC)C.[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1.[Pd]>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][NH:6][C:7]1[C:12]([NH:13][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:11][CH:10]=[CH:9][N:8]=1)[CH3:2]

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 14062544Ethyl 2-[(3-nitropyridin-2-YL)amino]acetate

Product 1

HCID 14390484HCID 14390484, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-(3-nitro-2-pyridinyl)glycine ethyl ester (1.0 g, 0.0044 mole) in 140 ml of tetrahydrofuran was hydrogenated over 5% palladium on carbon (0.2 g) at room temperature for 4 hr. The reaction mixture was dried over magnesium sulfate and filtered through a Celite pad. To this stirred solution was added triethylamine (0.6 g, 0.0059 mole) and benzoyl chloride (0.62 g, 0.0044 mole). The reaction mixture was allowed to stir at room temperature overnight. The triethylamine hydrochloride was filtered off and the filtrate was evaporated to dryness. The residue was taken up in ether-methylene chloride solution. Sodium sulfate was added to adsorb an immiscible dark oil. The filtrate was evaporated to dryness to give a residue which was recrystallized from ether. The precipitate was collected, washed with a solution of 75% hexanes/25% ether, and dried at room temperature under high vacuum to yield 1.1 g, of title compound, m.p. 115°-16° C.

Workup

  1. dry with materialThe reaction mixture was dried over magnesium sulfate
  2. filtrationfiltered through a Celite pad
  3. filtrationThe triethylamine hydrochloride was filtered off
  4. customthe filtrate was evaporated to dryness
  5. additionSodium sulfate was added
  6. customThe filtrate was evaporated to dryness
  7. customto give a residue which
  8. customwas recrystallized from ether
  9. customThe precipitate was collected
  10. washwashed with a solution of 75% hexanes/25% ether
  11. customdried at room temperature under high vacuum
  12. customto yield 1.1 g

Sources & evidence

ORD record
ord-4c2c325a8a13488e95f9f8e81e8129aa
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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