Water → HCID 23434665, compound

HRID 1632844Notes

Reaction equation

HRID 1632844 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[C:14](Cl)(=[O:16])[CH3:15].[OH-].[K+].O>C(O)C>[C:14]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12])(=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 14797Potassium HydroxideHCID 1387234-Hydroxy-3-Nitroacetophenone

Product 1

HCID 23434665HCID 23434665, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture containing 36.2 g (0.2 mole) of 4'-hydroxy-3'-nitroacetophenone, 15.7 g of acetyl chloride, 22 mL of 50% KOH solution, 200 mL of H2O and 300 mL of 95% ethanol is stirred and heated to reflux for 18 hours. The mixture is evaporated to remove ethanol, and the aqueous mixture is extracted with CHCl3 to solubilize the product. The CHCl3 extract is evaporated to dryness to afford 4'-acetoxy-3'-nitroacetophenone, which is brominated with an equimolar quantity of Br2 in CHCl3 (100 mL) to afford 2-bromo-4'-acetoxy-3-nitroacetophenone. This phenacyl bromide is then reacted in 100 mL of ethanol with 2 equivalents of isopropylamine to afford 4'-acetoxy-3'-nitro-2-isopropylaminoacetophenone, which isolated as the hydrochloride by the procedure reported by Larson et al. in Journal of Medicinal Chemistry, 10, 467 (1967) for a related compound. This ketoamine is then hydrogenated in 90% aqueous ethanol with 0.5 g of 10% Pd-C/3.5 kg/cm2H2 pressure in a Parr hydrogenator until the uptake of H2 is completed. The mixture is filtered, and the filtrate is evaporated to dryness to afford the crude title compound.

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 hours
  3. customThe mixture is evaporated
  4. customto remove ethanol
  5. extractionthe aqueous mixture is extracted with CHCl3
  6. extractionThe CHCl3 extract
  7. customis evaporated to dryness

Sources & evidence

ORD record
ord-444f635957464c839e9bcadffbe925fb
Source dataset
uspto-grants-1984_10
Patent number
US04477680

Reaction notes

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