Acetic Anhydride → HCID 20313028, compound

HRID 2420101Notes

Reaction equation

HRID 2420101 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]([O:17][CH3:18])=[O:16])=[N:13][CH:14]=2)=[CH:6][CH:5]=1)([O-])=O.[C:21](OC(=O)C)(=[O:23])[CH3:22]>[C].[Pd].C(O)(=O)C>[NH:1]([C:4]1[CH:20]=[CH:19][C:7]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]([O:17][CH3:18])=[O:16])=[N:13][CH:14]=2)=[CH:6][CH:5]=1)[C:21]([CH3:22])=[O:23]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 20313017HCID 20313017, compound

Product 1

HCID 20313028HCID 20313028, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

3.0 Grams of methyl 5-(4-nitrobenzyl)picolinate were dissolved in 150 ml. of a mixture of acetic acid and acetic anhydride (4:1). The resulting solution was added with 6.0 g of 5% palladium-carbon. Catalytic reduction was carried out at room temperature under atmospheric pressure. After 1.5 hours, the reaction solution was subjected to filtration and the filtrate was concentrated under reduced pressure. The residue was added with n-hexane to form crystals. The crystals were recrystallized from a solvent comprising a mixture of chloroform/n-hexane to obtain 1.5 g of methyl 5-(4-acetaminobenzyl)picolinate.

Workup

  1. customwas carried out at room temperature under atmospheric pressure
  2. filtrationthe reaction solution was subjected to filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionThe residue was added with n-hexane
  5. customto form crystals
  6. customThe crystals were recrystallized from a solvent comprising
  7. additiona mixture of chloroform/n-hexane

Sources & evidence

ORD record
ord-443beaa7f8304033ad9c78f2d093ddd6
Source dataset
uspto-grants-1978_08
Patent number
US04109000

Reaction notes

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