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

HRID 2171528Notes

Reaction equation

HRID 2171528 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-15240f5ff4f543229c07fb80c55ee900
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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