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

HRID 57682Notes

Reaction equation

HRID 57682 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 26A) were dissolved in 285 ml of 4N 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-4f1cf7432fbc47c287ad6e3de530ad74
Source dataset
uspto-grants-2016_09
Patent number
US09434731B2

Reaction notes

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