Benzene--cyclohexane (1/1) → 3-ethyl-5-nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazine

HRID 589059

반응식

HRID 589059 반응식
[CH2:1]([Li])[CH3:2].C1C=CC=CC=1.C1CCCCC1.[N+:16]([C:19]1[C:24]2[N:25]=[C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)[CH2:27][O:28][C:23]=2[CH:22]=[CH:21][CH:20]=1)([O-:18])=[O:17]>O1CCCC1>[CH2:1]([C:26]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[NH:25][C:24]2[C:19]([N+:16]([O-:18])=[O:17])=[CH:20][CH:21]=[CH:22][C:23]=2[O:28][CH2:27]1)[CH3:2]

참가 물질

5

반응물 3

HCID 18624872Benzene--cyclohexane (1/1)HCID 904089025-nitro-3-pyridin-2-yl-2H-1,4-benzoxazineHCID 178506846HCID 178506846, 화합물

생성물 1

HCID 904093673-ethyl-5-nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

0.5 M Ethyl lithium in benzene-cyclohexane (1.8 mL, 0.88 mmol) was added drop-wise to a solution of 5-nitro-3-pyridin-2-yl-2H-1,4-benzoxazine (0.025 g, 0.88 mmol) in tetrahydrofuran (4 mL), cooled to −78° C. The reaction was stirred for 1 h at −78° C. and was then quenched with methanol. The reaction mixture was partitioned between ethyl acetate and water, and the organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to give crude product. The product was purified by FCC on silica gel eluting a hexane:ethyl acetate gradient to give 3-ethyl-5-nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazine as a solid (0.021 g. 84%). LCMS calculated for C15H16N3O3 (M+H)+: m/z=286.1. found: 286.0.

후처리

  1. customwas then quenched with methanol
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washthe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give crude product
  8. customThe product was purified by FCC on silica gel eluting a hexane

출처 및 근거

ORD 기록
ord-201ae97b463f4655806c488d4a39f5b9
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227985B2

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