Sodium Bicarbonate → 4'-Acetamido-2-hydroxyacetophenone

HRID 32471

Reaction equation

HRID 32471 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:14])[CH2:12]Br)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C([O-])=[O:16].[K+].C(=O)(O)[O-].[Na+]>CCO>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:14])[CH2:12][OH:16])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2735122Potassium FormateHCID 12364739N-[4-(2-Bromoacetyl)Phenyl]Acetamide

Product 1

HCID 221825304'-Acetamido-2-hydroxyacetophenoneYield 95.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
38 °C

Procedure

To a suspension of 4′-acetamido-2-bromoacetophenone 3 (10.0 g, 39 mmol) in EtOH (800 mL), aqueous potassium formate (35.4 g in 200 mL) was added then followed by sodium bicarbonate (3.68 g). The mixture was stirred at 38° C. (inner temp.) for 22 h. The mixture was evaporated in vacuo until the total volume reached to ca. 300 mL The mixture was diluted with ethyl acetate (1200 mL), washed with water (200 mL), then brine (2×400 mL). Aqueous layers were extracted with ethyl acetate (800 mL then 400 mL). Combined organic layer was dried over anhydrous sodium sulfate and then evaporated in vacuo to give crude 4 as a solid (7.17 g, 95%) which was used to the next step without any purification. MS(ES) m/e 194 [M+H].

Workup

  1. additionwas added
  2. customThe mixture was evaporated in vacuo until the total volume
  3. additionwas diluted with ethyl acetate (1200 mL)
  4. washwashed with water (200 mL)
  5. extractionAqueous layers were extracted with ethyl acetate (800 mL
  6. dry with materialCombined organic layer was dried over anhydrous sodium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-e9b276f7adcf4e6382135009aea5fa2d
Source dataset
uspto-grants-2008_09
Patent number
US07427623B2

Linked notes

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