Potassium Cyanide → 5-nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazine-3-carbonitrile

HRID 589063노트

반응식

HRID 589063 반응식
[C-:1]#[N:2].[K+].[N+:4]([C:7]1[C:12]2[N:13]=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:15][O:16][C:11]=2[CH:10]=[CH:9][CH:8]=1)([O-:6])=[O:5]>C(#N)C>[N+:4]([C:7]1[C:12]2[NH:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)([C:1]#[N:2])[CH2:15][O:16][C:11]=2[CH:10]=[CH:9][CH:8]=1)([O-:6])=[O:5]

참가 물질

4

반응물 2

HCID 9032Potassium CyanideHCID 904089025-nitro-3-pyridin-2-yl-2H-1,4-benzoxazine

생성물 1

HCID 904101505-nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazine-3-carbonitrile

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Potassium cyanide (500 mg, 7 mmol) was added to a solution of 5-nitro-3-pyridin-2-yl-2H-1,4-benzoxazine (1 g, 4 mmol) (Example 70, Step 1), in acetonitrile (20 mL), and was stirred overnight at room temperature. The reaction was partitioned between ethyl acetate and water, and the organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to give the crude product. The product was crystallized from methylene chloride to give 5-nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazine-3-carbonitrile as a dark yellow powder (0.60 g. 60%). LCMS calculated for C14H11N4O3 (M+H)+: m/z=283.1. found: 282.9.

후처리

  1. customThe reaction was partitioned between ethyl acetate and water
  2. washthe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product
  7. customThe product was crystallized from methylene chloride

출처 및 근거

ORD 기록
ord-b904f1080dd840b5b8c47410b86b2b8d
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227985B2

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