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

HRID 589063Notes

Reaction equation

HRID 589063 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b904f1080dd840b5b8c47410b86b2b8d
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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