Acetic Anhydride → 5-Acetylamino-2-amino-4-picoline

HRID 1740935Notes

Reaction equation

HRID 1740935 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH2:9])=[CH:4][N:3]=1.C(N(CC)CC)C.[C:17](OC(=O)C)(=[O:19])[CH3:18]>C(Cl)Cl>[C:17]([NH:9][C:5]1[C:6]([CH3:8])=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=1)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 27344282,5-Diamino-4-picoline

Product 1

HCID 98989245-Acetylamino-2-amino-4-picoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,5-diamino-4-picoline, prepared as shown in Example 30, (50 mg, 0.41 mmol) in methylene chloride (1.0 mL) were added triethylamine (70 uL, 0.49 mmol) and acetic anhydride (43 uL, 0.45 mmol). After stirring 0.5 h at room temperature, the reaction mixture 25 was evaporated to dryness and purified by silica gel chromatography using 40:10:1 chloroform-methanol-water as eluant to give the title compound.

Workup

  1. customthe reaction mixture 25 was evaporated to dryness
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-fdc3cb295b524e8b8b6628aacb1d18ff
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

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