Hydrochloric Acid → 3,4-dihydro-4-(2-hydroxy-2-phenylethyl)-2,2-dimethyl-6-nitro-2H-1,4-benzoxazine

HRID 37107노트

반응식

HRID 37107 반응식
[CH3:1][C:2]1([CH3:25])[C:7](=O)[N:6]([CH2:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])[C:5]2[CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=[CH:21][C:4]=2[O:3]1.B.CO.Cl>O1CCCC1>[OH:11][CH:10]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:9][N:6]1[C:5]2[CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=[CH:21][C:4]=2[O:3][C:2]([CH3:25])([CH3:1])[CH2:7]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6331BoraneHCID 107358923,4-dihydro-2,2-dimethyl-6-nitro-3-oxo-4-phenacyl-2H-1,4-benzoxazine

생성물 1

HCID 106877203,4-dihydro-4-(2-hydroxy-2-phenylethyl)-2,2-dimethyl-6-nitro-2H-1,4-benzoxazine수율 115.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

In an argon gas stream, 1.5 g of 3,4-dihydro-2,2-dimethyl-6-nitro-3-oxo-4-phenacyl-2H-1,4-benzoxazine was added to 30 ml of a 1.0 M solution of borane in tetrahydrofuran at 0°-10° C. The above solution was stirred at 70° C. for 1 hour, at the end of which time 5.6 ml of methanol was gradually added. After stirring at 70° C. for 15 minutes, 5.6 ml of concentrated hydrochloric acid was added and the mixture was further stirred at 70° C. for 1 hour. The solvent was then distilled off and the residue was diluted with 30 ml of water, made alkaline with potassium carbonate, and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was distilled off. The residue was purified by silica gel column chromatography (eluent: ethyl acetate-n-hexane) to give 1.67 g of 3,4-dihydro-4-(2-hydroxy-2-phenylethyl)-2,2-dimethyl-6-nitro-2H- 1,4-benzoxazine as oil.

후처리

  1. additionwas gradually added
  2. stirringthe mixture was further stirred at 70° C. for 1 hour
  3. distillationThe solvent was then distilled off
  4. additionthe residue was diluted with 30 ml of water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate-n-hexane)

출처 및 근거

ORD 기록
ord-2897d63c137948458c08aedaa03d0415
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420126

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