4-Methylmorpholine → HCID 18996967、化合物

HRID 374654ノート

反応式

HRID 374654 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 18996967HCID 18996967、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-15 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ca470bc8b7d4497bb261b7e10ce07e77
出典データセット
uspto-grants-1996_01
特許番号
US05480873

反応ノート

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