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

HRID 2389790Notes

Reaction equation

HRID 2389790 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.C(O)C.C([O-])(=O)C.[Na+].Cl.[NH2:27][OH:28]>O>[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:27][OH:28])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 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 962WaterSolvent2×

Procedure

15.45 g (60.2 mmol) of tert-butyl (6-chloro-3-formylpyridin-2-yl)carbamate (Example 106A) are introduced into 750 ml of ethanol, and a solution of 225 ml of water and 9.38 g (120.4 mmol) of sodium acetate is added and stirred for 5 min. A solution of 225 ml of water and 8.36 g (114.4 mmol) of hydroxylamine hydrochloride is added, and the mixture is stirred at RT for 4 h. The reaction mixture is concentrated in a rotary evaporator at 20° C. The residue is taken up in ethyl acetate and washed twice with saturated sodium hydroxide carbonate solution and once with saturated sodium chloride solution. The organic phase is separated off, dried over magnesium sulphate and concentrated in a rotary evaporator at 20° C. 15.5 g (80% of theory) of the product are obtained as a solid.

Workup

  1. stirringthe mixture is stirred at RT for 4 h
  2. concentrationThe reaction mixture is concentrated in a rotary evaporator at 20° C
  3. washwashed twice with saturated sodium hydroxide carbonate solution and once with saturated sodium chloride solution
  4. customThe organic phase is separated off
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated in a rotary evaporator at 20° C
  7. custom15.5 g (80% of theory) of the product are obtained as a solid

Sources & evidence

ORD record
ord-9f121029f8a547d9b8d9b7268707ca4c
Source dataset
uspto-grants-2012_09
Patent number
US08273752B2

Reaction notes

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