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

HRID 1182989Notes

Reaction equation

HRID 1182989 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 2A) were initially charged in 750 ml of ethanol and admixed with a solution of 225 ml of water and 9.38 g (120.4 mmol) of sodium acetate and 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. At 20° C., the reaction mixture was concentrated on a rotary evaporator. The residue was taken up in ethyl acetate and washed twice with saturated sodium hydrogencarbonate solution and once with saturated sodium chloride solution. The organic phase was removed, dried over magnesium sulphate and concentrated at 20° C. on a rotary evaporator. 15.5 g (80% of theory) of the product were obtained in solid form.

Workup

  1. stirringthe mixture was stirred at RT for 4 h
  2. concentrationAt 20° C., the reaction mixture was concentrated on a rotary evaporator
  3. washwashed twice with saturated sodium hydrogencarbonate solution and once with saturated sodium chloride solution
  4. customThe organic phase was removed
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated at 20° C. on a rotary evaporator
  7. custom15.5 g (80% of theory) of the product were obtained in solid form

Sources & evidence

ORD record
ord-3569483b9c6f4abe9af260562e7d9108
Source dataset
uspto-grants-2014_03
Patent number
US08664246B2

Reaction notes

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