4-Methylmorpholine → HCID 18996984, compound

HRID 374653Notes

Reaction equation

HRID 374653 reaction equation
[C:1]([O:4][C:5]1[C:18]2[C:17](=[O:19])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:20][C:21](=[O:23])[CH3:22])[C:10](=[O:24])[C:9]=2[CH:8]=[C:7]([C:25](O)=[O:26])[CH:6]=1)(=[O:3])[CH3:2].CN1CCOCC1.C(OC(Cl)=O)C(C)C.Cl.[CH2:44]([O:51][NH2:52])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>CN(C)C=O>[CH2:44]([O:51][NH:52][C:25]([C:7]1[CH:6]=[C:5]([O:4][C:1](=[O:3])[CH3:2])[C:18]2[C:17](=[O:19])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:20][C:21](=[O:23])[CH3:22])[C:10](=[O:24])[C:9]=2[CH:8]=1)=[O:26])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 26248DiacereinHCID 62365Isobutyl chloroformateHCID 102312Benzyloxyamine hydrochloride

Product 1

HCID 18996984HCID 18996984, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent4×

Conditions

Temperature
-15 °C

Procedure

To a stirred solution of 4,5-diacetoxy-9,10-dihydro-9,10-dioxoanthracene-2-carboxylic acid (6.14 g) in dry dimethylformamide (1.1 l) and nitrogen at -15° C. was added dropwise N-methylmorpholine (3.71 g) as a solution in dimethylformamide (20 ml) during 5 minutes. Stirring at -15° C. was continued for 40 minutes before the dropwise addition of isobutylchloroformate (2.51 g) as a solution in dimethylformamide (10 ml) over 10 minutes. The mixture was stirred at -15° C. for 45 minutes when a solution of O-benzylhydroxylamine hydrochloride (2.93 g) in dimethylformamide (20 ml) was added dropwise. Stirring was continued for 5 hours at -15° C. and the mixture was then allowed to warm to room temperature. After 16 hours at room temperature, the dark solution was concentrated in vacuo. The gummy residue was triturated with ethyl acetate to yield a bright yellow solid. This was triturated with tetrahydrofuran and the insoluble material then washed with 5% aqueous sodium bicarbonate solution. The insoluble yellow solid was washed with water and dried in vacuo yielding the title compound, m.p. 192°-194° C.

Workup

  1. additionwas added dropwise
  2. stirringStirring
  3. temperatureto warm to room temperature
  4. waitAfter 16 hours at room temperature
  5. concentrationthe dark solution was concentrated in vacuo
  6. customThe gummy residue was triturated with ethyl acetate
  7. customto yield a bright yellow solid
  8. customThis was triturated with tetrahydrofuran
  9. washthe insoluble material then washed with 5% aqueous sodium bicarbonate solution
  10. washThe insoluble yellow solid was washed with water
  11. customdried in vacuo

Sources & evidence

ORD record
ord-4372405043c54980b5c320d0ec811f43
Source dataset
uspto-grants-1996_01
Patent number
US05480873

Reaction notes

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