Acetone → HCID 90409561, compound

HRID 589052Notes

Reaction equation

HRID 589052 reaction equation
Br.Br[CH2:3][C:4]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:5].[NH2:12][C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=1[OH:22].C(=O)([O-])[O-].[K+].[K+].CC(C)=O>O>[NH2:12][C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=1[O:22][CH2:3][C:4]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:5]

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 27762343-(2-Bromoacetyl)pyridine hydrobromideHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 90409561HCID 90409561, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Bromo-1-(pyridin-3-yl)ethanone hydrobromide (600 mg, 2 mmol) (HBr salt) was added to a mixture of 2-amino-3-nitrophenol (300 mg, 2 mmol) and potassium carbonate (400 mg, 3 mmol) in acetone (30 mL, 400 mmol) at room temperature. The reaction was stirred at room temperature for 18 h, was diluted with water, and was then extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated to give crude 2-(2-amino-3-nitrophenoxy)-1-pyridin-3-ylethanone (0.35 g, 60%). LCMS calculated for C13H12N3O4 (M+H)+: m/z=274.1. found: 274.1.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2078d78de8b14b6aac1927ed452f5a05
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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