Ethanol → HCID 13282598, compound

HRID 1388283Notes

Reaction equation

HRID 1388283 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([OH:10])[C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[CH2:19](O)[CH3:20]>Cl>[CH2:19]([O:8][C:7](=[O:9])[C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:5]1[CH:17]=[CH:18][C:2]([NH2:1])=[CH:3][CH:4]=1)[OH:10])[CH3:20]

Participants

4

Reactant 2

HCID 702EthanolHCID 13282597HCID 13282597, compound

Product 1

HCID 13282598HCID 13282598, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4.8 g (19.7 mmol) of 4-aminobenzilic acid was dissolved in 200 ml of absolute ethanol (EtOH) saturated with dry HCl gas. The reaction mixture was refluxed for 24 hours then spin evaporated to dryness in vacuum. The residue was dissolved in water and neutralized with NaHCO3, extracted with 2×50 ml of AcOEt, washed with water (2×) and the AcOEt extract filtered through a siliconized filter and dried over MgSO4. The dried solution was filtered and spin evaporated in vacuum. Yellow oil, 2.8 g (52%). SGTLC in acetone Rf 0.8. HPLC Bondapak μC18MeOH/H2O (75:25) pH 4 (formic acid). Elemental Analysis Calc. for C16H17NO3. Calc. C 70.83, H 6.32, N 5.16; Found C 70.77, H 6.47, N 5.04, 5.26.

Workup

  1. temperatureThe reaction mixture was refluxed for 24 hours
  2. customthen spin evaporated to dryness in vacuum
  3. dissolutionThe residue was dissolved in water and neutralized with NaHCO3
  4. extractionextracted with 2×50 ml of AcOEt
  5. washwashed with water (2×)
  6. extractionthe AcOEt extract
  7. filtrationfiltered through
  8. filtrationa siliconized filter
  9. dry with materialdried over MgSO4
  10. filtrationThe dried solution was filtered
  11. customspin evaporated in vacuum

Sources & evidence

ORD record
ord-f8bd97cc6ee647a19a7d3154ff97667a
Source dataset
uspto-grants-1984_02
Patent number
US04431627

Reaction notes

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