Benzyl Bromide → 5-[(Benzyloxy)carbonyl]nicotinic acid

HRID 860473

反応式

HRID 860473 の反応式
[H-].[Na+].[N:3]1[CH:8]=[C:7]([C:9]([OH:11])=[O:10])[CH:6]=[C:5]([C:12]([OH:14])=[O:13])[CH:4]=1.Br[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:16]([O:10][C:9]([C:7]1[CH:8]=[N:3][CH:4]=[C:5]([CH:6]=1)[C:12]([OH:14])=[O:13])=[O:11])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 103663,5-Pyridinedicarboxylic acidHCID 24758Sodium hydride

生成物 1

HCID 574445445-[(Benzyloxy)carbonyl]nicotinic acid収率 23.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a suspension of 60% sodium hydride (527 mg) in dimethylformamide (20 mL) was added 3,5-pyridinedicarboxylic acid (2.00 g) under ice-water cooling and the mixture was stirred at 0° C. for 1 hour. To the mixture was added (bromomethyl)benzene (2.05 g) and the mixture was stirred at 60° C. for 2 hours. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was triturated with ethyl acetate to give 5-[(benzyloxy)carbonyl]nicotinic acid as a pale yellow powder (722 mg).

後処理

  1. stirringthe mixture was stirred at 60° C. for 2 hours
  2. customThe mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was triturated with ethyl acetate

出典と根拠

ORDレコード
ord-73d806606503471c8e06e8a873b009fc
出典データセット
uspto-grants-2006_12
特許番号
US07153854B2

関連ノート

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