Dimethylformamide → HCID 21264502, compound

HRID 566960Notes

Reaction equation

HRID 566960 reaction equation
O[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6]C=CN=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:17](Br)[CH:18]=[CH2:19].[CH3:21][N:22]([CH:24]=[O:25])C>>[CH2:17]([O:25][C:24]1[CH:2]=[C:7]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:21][N:22]=1)[CH:18]=[CH2:19]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 178526677HCID 178526677, compound

Product 1

HCID 21264502HCID 21264502, compoundYield 94%

Procedure

To a solution of 2-hydroxy-3-nitropyridine (30.5 mmol) in DMF (20 ml), cesium carbonate (45.7 mmol) and allyl bromide (3.15 mL, 35.6 mmol) were added. The reaction mixture was stirred at room temperature for 18 hours, then it was partitioned between ethyl acetate and water. The combined organic phase was dried and concentrated to give the desired product (5.85 g, 94%). EI-MS m/z 205 (M+).

Workup

  1. customit was partitioned between ethyl acetate and water
  2. customThe combined organic phase was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7053c91a76b541c89ba23791530636a4
Source dataset
uspto-grants-2001_01
Patent number
US06177448B1

Reaction notes

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