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

HRID 589059

反応式

HRID 589059 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-201ae97b463f4655806c488d4a39f5b9
出典データセット
uspto-grants-2016_01
特許番号
US09227985B2

関連ノート

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