Water → tert-Butyl{6-chloro-3-[(hydroxyimino)methyl]pyridin-2-yl}carbamate

HRID 57681Notes

Reaction equation

HRID 57681 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:5]([CH:16]=O)=[CH:4][CH:3]=1.[OH2:18].C([O-])(=O)C.[Na+].Cl.[NH2:25]O>C(O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:5]([CH:16]=[N:25][OH:18])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 51051664tert-butyl N-(6-chloro-3-formylpyridin-2-yl)carbamate

Product 1

HCID 76639260tert-Butyl{6-chloro-3-[(hydroxyimino)methyl]pyridin-2-yl}carbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

15.45 g (60.2 mmol) of tert-butyl (6-chloro-3-formylpyridin-2-yl)carbamate (Example 25A) were initially charged in 750 ml of ethanol, a solution of 225 ml of water and 9.38 g (120.4 mmol) of sodium acetate was added and the mixture was stirred for 5 min. A solution of 225 ml of water and 8.36 g (114.4 mmol) of hydroxylamine hydrochloride was added and the mixture was stirred at RT for 4 h. The reaction mixture was concentrated on a rotary evaporator at 20° C. The residue was taken up in ethyl acetate, washed twice with saturated sodium bicarbonate solution and once with saturated sodium chloride solution. The organic phase was separated off, dried over magnesium sulfate and concentrated on a rotary evaporator at 20° C. This gave 15.5 g (80% of theory) of the product as a solid.

Workup

  1. stirringthe mixture was stirred at RT for 4 h
  2. concentrationThe reaction mixture was concentrated on a rotary evaporator at 20° C
  3. washwashed twice with saturated sodium bicarbonate solution and once with saturated sodium chloride solution
  4. customThe organic phase was separated off
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated on a rotary evaporator at 20° C

Sources & evidence

ORD record
ord-56a80dbdfe504aec8a7a6f2e11cb60c2
Source dataset
uspto-grants-2016_09
Patent number
US09434731B2

Reaction notes

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