4-Methylmorpholine → HCID 18996967, compound

HRID 374654Notes

Reaction equation

HRID 374654 reaction equation
[CH3:1][O:2][C:3]1[C:16]2[C:15](=[O:17])[C:14]3[C:9](=CC=[CH:12][C:13]=3OC)[C:8](=[O:20])[C:7]=2[CH:6]=[C:5]([C:21]([OH:23])=O)[CH:4]=1.CN1[CH2:30][CH2:29][O:28][CH2:27]C1.C(OC(Cl)=O)C(C)C.Br.[CH3:40][NH:41][O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>O1CCCC1>[CH2:43]([O:42][N:41]([CH3:40])[C:21]([C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:16]2[C:15](=[O:17])[C:30]3[C:9](=[CH:14][CH:13]=[CH:12][C:29]=3[O:28][CH3:27])[C:8](=[O:20])[C:7]=2[CH:6]=1)=[O:23])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 99727772-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dimethoxy-9,10-dioxo-HCID 18997025HCID 18997025, compound

Product 1

HCID 18996967HCID 18996967, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-15 °C

Procedure

To a stirred solution of 9,10-dihydro-4,5-dimethoxy-9,10-dioxoanthracene-2-carboxylic acid (2.00 g) in tetrahydrofuran (900 ml) at room temperature under nitrogen was added N-methyl morpholine (1.36 g) dropwise. The solution was then cooled to -15° C. and a solution of isobutylchloroformate (0.92 g) in tetrahydrofuran (5 ml) added during 5 minutes. The clear solution became cloudy. The mixture was stirred at -15° C. for 1 hour. To this was added portionwise over 5 minutes N-methyl O-benzylhydroxylamine hydrobromide (1.50 g). The cloudy mixture was stirred at -15° C. for 3 hours and then allowed to warm to room temperature. After 16 hours at room temperature, the mixture was filtered and the filtrate concentrated in vacuo. The resulting yellow solid was taken up in ethyl acetate (800 ml) and filtered to remove insolubles. The solution was washed with 10% aqueous sodium carbonate solution (three times), water (twice), dried (MgSO4), filtered and evaporated to yield the title compound as a bright yellow powder, m.p. 170°-171° C.

Workup

  1. stirringThe cloudy mixture was stirred at -15° C. for 3 hours
  2. temperatureto warm to room temperature
  3. waitAfter 16 hours at room temperature
  4. filtrationthe mixture was filtered
  5. concentrationthe filtrate concentrated in vacuo
  6. filtrationfiltered
  7. customto remove insolubles
  8. washThe solution was washed with 10% aqueous sodium carbonate solution (three times), water (twice),
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-ca470bc8b7d4497bb261b7e10ce07e77
Source dataset
uspto-grants-1996_01
Patent number
US05480873

Reaction notes

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