2'-Hydroxyacetophenone → HCID 19755424, compound

HRID 1588231Notes

Reaction equation

HRID 1588231 reaction equation
[CH:1]([NH:3][CH2:4][C:5](=[O:7])[CH3:6])=[O:2].O[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15](=[O:17])[CH3:16].N1CCCC1>C1(C)C=CC=CC=1>[CH3:6][C:5]1([CH2:4][NH:3][CH:1]=[O:2])[CH2:16][C:15](=[O:17])[C:10]2[C:9](=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:7]1

Participants

5

Reactant 3

HCID 83752'-HydroxyacetophenoneHCID 31268PyrrolidineHCID 14715945N-(2-Oxopropyl)formamide

Product 1

HCID 19755424HCID 19755424, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

20.2 g (0.2 mol) of formylaminoacetone [A. Treibs u.a., Chem. Ber. 84 96 (1951)] and 27.2 g (0.2 mol) of o-hydroxyacetophenone are dissolved in 100 ml of toluene, and 10 ml of pyrrolidine are added. The mixture is stirred at 25° C. for 20 hours and then at 115° C. for 2 hours. After cooling, the mixture is extracted by shaking successively with 2N HCl, 2N NaOH and water, the organic phase is concentrated and the 2-methyl-2-formylaminomethylchroman-4-one formed is isolated by chromatography. Melting point: 96°-8° C.

Workup

  1. waitat 115° C. for 2 hours
  2. temperatureAfter cooling
  3. extractionthe mixture is extracted
  4. stirringby shaking successively with 2N HCl, 2N NaOH and water
  5. concentrationthe organic phase is concentrated

Sources & evidence

ORD record
ord-eaf490509c334c489853ace90b354ca4
Source dataset
uspto-grants-1993_06
Patent number
US05221681

Reaction notes

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