Sodium Hydroxide → 5-Bromopyridine-2-carbonitrile

HRID 72394

反応式

HRID 72394 の反応式
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]([NH2:15])=O)=[N:11][CH:12]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]#[N:15])=[N:11][CH:12]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 7351515-Bromopyridine-2-carboxamide

生成物 1

HCID 8171545-Bromopyridine-2-carbonitrile収率 82.7%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Phosphorus oxychloride (111 g, 0.720 mol) was added to a mixture of 5-bromopicolinamide (D8) (58 g, 0.288 mol) in dry toluene (300 ml) The mixture was heated to reflux for 2 hours. The mixture was poured into ice/water, and basified to pH=12 with 2N NaOH. The resulting mixture was extracted with ethyl acetate and the organic phase was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture petroleum ether/ethyl acetate 10:1. Collected fractions, after solvent evaporation afforded the title compound (D9) (43.6 g) as a yellow solid.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washthe organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel eluting with a mixture petroleum ether/ethyl acetate 10:1
  8. customCollected fractions, after solvent evaporation

出典と根拠

ORDレコード
ord-e83cf6404d21478aac0b005324c1ef0e
出典データセット
uspto-grants-2014_09
特許番号
US08828987B2

関連ノート

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