Water → 2-(Pivaloylamino)pyridine

HRID 1607563Notes

Reaction equation

HRID 1607563 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.C(N(CC)CC)C.O>C(Cl)Cl>[C:1]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 104392-AminopyridineHCID 62493Pivaloyl chloride

Product 1

HCID 10515192-(Pivaloylamino)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of pivaloyl chloride (96 g) in methylene chloride (200 ml) is added dropwise to a cooled mixture of 2-aminopyridine (50 g) and triethylamine (108 g) in methylene chloride (650 ml). The reaction mixture is stirred overnight at RT and poured into water which is basified and the organic layer separated and concentrated in vacuo. Hexane is added to the oil which results in the precipitation of a crystalline solid which is filtered and the solid taken up in aqueous acid. The desired pyridine compound is recrystallized as a white crystalline solid.

Workup

  1. customthe organic layer separated
  2. concentrationconcentrated in vacuo
  3. additionHexane is added to the oil which
  4. customresults in the precipitation of a crystalline solid which
  5. filtrationis filtered
  6. customThe desired pyridine compound is recrystallized as a white crystalline solid

Sources & evidence

ORD record
ord-a14f5d9232904da497ebb41834507055
Source dataset
uspto-grants-1989_09
Patent number
US04866074

Reaction notes

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