Acetic Anhydride → HCID 178467639, compound

HRID 1077297Notes

Reaction equation

HRID 1077297 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH2:8]([O:10][C:11]([C:13]1[CH:14]=[N:15][C:16]2[CH:17]=[C:18]3[O:28][CH:27]([CH2:29][O:30][CH2:31][CH3:32])[CH2:26][O:25][C:19]3=[C:20]([NH2:24])[C:21]=2[C:22]=1[OH:23])=[O:12])[CH3:9]>C(O)C>[CH2:8]([O:10][C:11]([C:13]1[CH:14]=[N:15][C:16]2[CH:17]=[C:18]3[O:28][CH:27]([CH2:29][O:30][CH2:31][CH3:32])[CH2:26][O:25][C:19]3=[C:20]([NH:24][C:1](=[O:3])[CH3:2])[C:21]=2[C:22]=1[OH:23])=[O:12])[CH3:9]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178467640HCID 178467640, compound

Product 1

HCID 178467639HCID 178467639, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

3 portions of acetic acid anhydride totalling 3 ml were added at intervals of half an hour to a suspension of 0.13 g of 10-amino-3-(ethoxymethyl)-2,3-dihydro-9-hydroxy-p-dioxino [2,3-g] quinoline-8-carboxylic acid ethyl ester obtained by the method described in Example 29) in 15 ml of 96% ethanol. Before the last addition the reaction mixture was briefly heated to about 50°C, a clear solution being obtained. After the last addition the mixture was stirred for another hour and subsequently concentrated by evaporation in a vacuum. The concentrate was mixed with methylene chloride and water, after which the two layers were separated. The water layer was extracted 2 times with methylene chloride, the entire solution in methylene chloride was then washed thrice with water and subsequently dried over anhydrous sodium sulfate. Subsequently the solvent was distilled off in a vacuum. The residue having the superscribed structure was not purified any further.

Workup

  1. customobtained by the method
  2. additionBefore the last addition the reaction mixture
  3. customa clear solution being obtained
  4. additionAfter the last addition the mixture
  5. concentrationsubsequently concentrated by evaporation in a vacuum
  6. additionThe concentrate was mixed with methylene chloride and water
  7. customafter which the two layers were separated
  8. extractionThe water layer was extracted 2 times with methylene chloride
  9. washthe entire solution in methylene chloride was then washed thrice with water
  10. dry with materialsubsequently dried over anhydrous sodium sulfate
  11. distillationSubsequently the solvent was distilled off in a vacuum
  12. customwas not purified any further

Sources & evidence

ORD record
ord-3f75709db4e142ce828fa536a4e1d554
Source dataset
uspto-grants-1976_05
Patent number
US03959473

Reaction notes

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