Triethylamine → HCID 14390493, compound

HRID 2351593Notes

Reaction equation

HRID 2351593 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:17](Cl)(=[O:26])[C:18]1[C:19]([O:24][CH3:25])=[CH:20][CH:21]=[CH:22][CH:23]=1.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:17](=[O:26])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])=[CH:11][CH:10]=[CH:9][N:8]=1)[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 889692-Methoxybenzoyl chlorideHCID 14062544Ethyl 2-[(3-nitropyridin-2-YL)amino]acetate

Product 1

HCID 14390493HCID 14390493, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-(3-nitro-2-pyridinyl)glycine ethyl ester (64.4 g, 0.286 mole) in 900 ml of tetrahydrofuran was hydrogenated in a 2-liter Parr bottle over 5% palladium on carbon (6.5 g) at room temperature for 1 hour. The reaction mixture was dried over magnesium sulfate and filtered through a Celite pad. A 235-ml portion of the filtrate was used in this reaction. Under nitrogen atmosphere, o-anisoyl chloride (9.72 g, 0.057 mole) and triethylamine (6.33 g, 0.063 mole) were added dropwise simultaneously to the above-stirred filtrate at room temperature. The reaction mixture was allowed to stir overnight. The reaction mixture was filtered, and the filtrate was treated with Florisil® (30 g), and evaporated to a solid. The solid was recrystallized from hot tetrahydrofuran (minimum). The solid was filtered off, washed with cold tetrahydrofuran, and dried under high vacuum at room temperature to give 5.7 g of title compound, mp 111°-12° C.

Workup

  1. dry with materialThe reaction mixture was dried over magnesium sulfate
  2. filtrationfiltered through a Celite pad
  3. customA 235-ml portion of the filtrate was used in this reaction
  4. filtrationThe reaction mixture was filtered
  5. additionthe filtrate was treated with Florisil® (30 g)
  6. customevaporated to a solid
  7. customThe solid was recrystallized from hot tetrahydrofuran (minimum)
  8. filtrationThe solid was filtered off
  9. washwashed with cold tetrahydrofuran
  10. customdried under high vacuum at room temperature

Sources & evidence

ORD record
ord-c4195524589a4470b91fd0e757c28d64
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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