m-Chloroperbenzoic acid → HCID 178427935, compound

HRID 1069145Notes

Reaction equation

HRID 1069145 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:9])=[N:6][C:7]=1[CH3:8].ClC1C=C(C=CC=1)C(OO)=[O:15].OS([O-])=O.[Na+]>ClCCl>[ClH:1].[Cl:1][C:2]1[C:7]([CH3:8])=[N+:6]([O-:15])[C:5]([NH2:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acid2×HCID 122510072-Amino-5-chloro-6-methylpyridineHCID 23665763Sodium Bisulfite

Product 1

HCID 178427935HCID 178427935, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 110 g (666 mmol) of 5-chloro-6-methyl-pyridineamine (Kress, T. J.; Moore, L. L.; Costantino, S. M. J. Org. Chem. (1976) 41(1), pp 93-96) in 1 L of dichloromethane was added 164 g (666 mmol) of m-chloroperoxybenzoic acid. The mixture was stirred at room temperature overnight and 20 g more of m-chloroperoxybenzoic acid was added. The mixture was stirred 1 h and 50 mL of saturated aqueous NaHSO3 were added. The solvent was removed and the residue was taken up in 1L of 1N HCl. The insoluble solids were filtered and washed with 3N HCl. Solvent was removed from the aqueous filtrate to give a solid which was recrystallized from ethanol affording 56.9 g of 5-chloro-6-methyl-2-pyridinamine 1-oxide, hydrochloride as a white solid, mp>250° C.

Workup

  1. stirringThe mixture was stirred 1 h
  2. customThe solvent was removed
  3. filtrationThe insoluble solids were filtered
  4. washwashed with 3N HCl
  5. customSolvent was removed from the aqueous filtrate
  6. customto give a solid which
  7. customwas recrystallized from ethanol affording 56.9 g of 5-chloro-6-methyl-2-pyridinamine 1-oxide, hydrochloride as a white solid, mp>250° C.

Sources & evidence

ORD record
ord-65c50c077dc6452694e4b69002aae126
Source dataset
uspto-grants-2001_06
Patent number
US06251947B1

Reaction notes

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