m-Chloroperbenzoic acid → HCID 178427935, compound

HRID 478983

Reaction equation

HRID 478983 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 1 L 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-e4188206d6a54245861c2f086c3bf271
Source dataset
uspto-grants-2003_11
Patent number
US06642392B1

Linked notes

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