4-Methylmorpholine → HCID 18996967, 화합물

HRID 374654노트

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HRID 374654 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 18996967HCID 18996967, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-15 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ca470bc8b7d4497bb261b7e10ce07e77
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05480873

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