Triethylamine → HCID 14390504, compound

HRID 622929Notes

Reaction equation

HRID 622929 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].[Cl:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[Cl:27])[C:21](Cl)=[O:22].C(N(CC)CC)C>O1CCCC1.[Pd]>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][NH:6][C:7]1[C:12]([NH:13][C:21](=[O:22])[C:20]2[CH:24]=[CH:25][C:26]([Cl:27])=[C:18]([Cl:17])[CH:19]=2)=[CH:11][CH:10]=[CH:9][N:8]=1)[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 14062544Ethyl 2-[(3-nitropyridin-2-YL)amino]acetate

Product 1

HCID 14390504HCID 14390504, compoundYield 7.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-(3-nitro-2-pyridinyl)glycine ethyl ester (22.5 g, 0.1 mole) in 250 ml of tetrahydrofuran was hydrogenated in a small Parr bottle over 5% palladium on carbon (2.5 g) at room temperature for 1 hr. The reaction mixture was dried over magnesium sulfate and filtered through a Celite pad. Under nitrogen atmosphere, 3,4-dichlorobenzoyl chloride (20.95 g, 0.1 mole) and triethylamine (11.1 g, 0.11 mole) were added dropwise simultaneously to the above stirred filtrate at room temperature. After stirring overnight, the reaction mixture was filtered and the filtrate was evaporated to dryness. The residue was treated with acetone and water to obtain a crystalline solid, which was refrigerated overnight. The solid was collected by filtration, washed with water, and dried under high vacuum at 50° C. overnight (37.1 g). A 4-g sample was recrystallized from acetone/water and dried under high vacuum at 50° C. for 2 days to give 2.66 g of title compound, mp 137°-38° C.

Workup

  1. dry with materialThe reaction mixture was dried over magnesium sulfate
  2. filtrationfiltered through a Celite pad
  3. filtrationthe reaction mixture was filtered
  4. customthe filtrate was evaporated to dryness
  5. additionThe residue was treated with acetone and water
  6. customto obtain a crystalline solid, which
  7. waitwas refrigerated overnight
  8. filtrationThe solid was collected by filtration
  9. washwashed with water
  10. customdried under high vacuum at 50° C. overnight (37.1 g)
  11. customA 4-g sample was recrystallized from acetone/water
  12. customdried under high vacuum at 50° C. for 2 days

Sources & evidence

ORD record
ord-7495bf40429342e0b2984f19ea16c2a5
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

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