Pyridine → N-[(2-chlorophenyl)methyl]-N-hydroxy-2,2-dimethylpropanamide

HRID 1995479Notes

Reaction equation

HRID 1995479 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][NH:16][OH:17].N1C=CC=CC=1>C(Cl)Cl>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][N:16]([OH:17])[C:3](=[O:4])[C:2]([CH3:7])([CH3:6])[CH3:1]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 12811040N-(2-ChlorobenZyl)hydroxylamine

Product 1

HCID 13192549N-[(2-chlorophenyl)methyl]-N-hydroxy-2,2-dimethylpropanamideYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound was prepared in the manner of Example 1, Step C, using 6.0 grams (0.05 mole) of trimethylacetyl chloride, 9.5 grams (0.06 mole) of N-(2-chlorophenylmethyl)hydroxylamine (prepared in Example I, Step A), and 14.2 grams (0.18 mole) of pyridine in 60 ml of methylene chloride. The crude product was recrystallized from hexane to give 3.5 grams of N-(2-chlorophenyl)methyl-N-hydroxy-2,2-dimethylpropanamide; mp 100°-102°.

Workup

  1. customThis compound was prepared in the manner of Example 1, Step C
  2. customThe crude product was recrystallized from hexane

Sources & evidence

ORD record
ord-729d60b841474856b5e2b8814836c3f2
Source dataset
uspto-grants-1983_09
Patent number
US04405357

Reaction notes

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