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

HRID 2088645Notes

Reaction equation

HRID 2088645 reaction equation
C(OC(=O)[NH:7][C:8]1[C:13]([CH:14]=[N:15][OH:16])=[CH:12][CH:11]=[C:10]([Cl:17])[N:9]=1)(C)(C)C>Cl.O1CCOCC1>[ClH:17].[NH2:7][C:8]1[C:13]([CH:14]=[N:15][OH:16])=[CH:12][CH:11]=[C:10]([Cl:17])[N:9]=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 5A) were dissolved in 285 ml of 4 N hydrogen chloride in dioxane, and the mixture was stirred for 30 min. The reaction mixture was concentrated to half of its original volume, and the same amount of diethyl ether was added. The reaction mixture was stirred for 20 min, and the product was filtered off and washed with diethyl ether. This gave 11 g (94% of theory) of the product as a solid.

Workup

  1. concentrationThe reaction mixture was concentrated to half of its original volume
  2. additionthe same amount of diethyl ether was added
  3. stirringThe reaction mixture was stirred for 20 min
  4. filtrationthe product was filtered off
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-18f22f2601de4b5dbd84e0a6a267827b
Source dataset
uspto-grants-2013_05
Patent number
US08436003B2

Reaction notes

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