Hydrochloric Acid → 1-(5-Bromopyridin-2-yl)ethan-1-one

HRID 520347Notes

Reaction equation

HRID 520347 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:18])[CH2:9]NC(=O)OC(C)(C)C)=[N:6][CH:7]=1.Cl.O1CCOCC1.CO>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:18])[CH3:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 312751,4-DioxaneHCID 57561517tert-Butyl (2-(5-bromopyridin-2-yl)-2-oxoethyl)carbamate

Product 1

HCID 231453451-(5-Bromopyridin-2-yl)ethan-1-oneYield 140.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a reaction mixture of tert-butyl 2-(5-bromopyridin-2-yl)-2-oxoethylcarbamate (0.36 g, 1.142 mmol) in DCM was added 4 M hydrogen chloride in dioxane (2 ml, 8.00 mmol) and some MeOH. The reaction was stirred at rt for 3 hrs. The reaction mixture was concentrated to dryness to yield 2-amino-1-HCl salf of (5-bromopyridin-2-yl)ethanone (0.32 g) as a yellow solid. LC/MS (Cond. N-1): [M+H]+ 215.13, RT=0.945 min.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness

Sources & evidence

ORD record
ord-76babb79f08d4d45b0a94f579f7c2c34
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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