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

HRID 589063ノート

反応式

HRID 589063 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b904f1080dd840b5b8c47410b86b2b8d
出典データセット
uspto-grants-2016_01
特許番号
US09227985B2

反応ノート

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