tert-Butyl{6-chloro-3-[(hydroxyimino)methyl]pyridin-2-yl}carbamate → 2-Amino-6-chloropyridine-3-carbaldehyde oxime hydrochloride

HRID 1182990Notes

Reaction equation

HRID 1182990 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8]C(=O)OC(C)(C)C)[C:5]([CH:16]=[N:17][OH:18])=[CH:4][CH:3]=1>Cl.O1CCOCC1>[ClH:1].[NH2:8][C:6]1[C:5]([CH:16]=[N:17][OH:18])=[CH:4][CH:3]=[C:2]([Cl:1])[N:7]=1

Participants

4

Reactant 1

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

Product 1

HCID 866350212-Amino-6-chloropyridine-3-carbaldehyde oxime hydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

15.5 g (57 mmol) of tert-butyl {6-chloro-3-[(hydroxyimino)methyl]pyridin-2-yl}carbamate (Example 3A) were dissolved in 285 ml of 4 N hydrogen chloride in dioxane and stirred for a further 30 min. The reaction mixture was concentrated by half and the same amount of diethyl ether was added. The reaction mixture was stirred for a further 20 min and the product was filtered off and washed with diethyl ether. 11 g (94% of theory) of the product were obtained in solid form.

Workup

  1. concentrationThe reaction mixture was concentrated by half
  2. additionthe same amount of diethyl ether was added
  3. stirringThe reaction mixture was stirred for a further 20 min
  4. filtrationthe product was filtered off
  5. washwashed with diethyl ether
  6. custom11 g (94% of theory) of the product were obtained in solid form

Sources & evidence

ORD record
ord-55753557bc5341a7bf91bd37eaa8f4e7
Source dataset
uspto-grants-2014_03
Patent number
US08664246B2

Reaction notes

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