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

HRID 860473

반응식

HRID 860473 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-73d806606503471c8e06e8a873b009fc
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153854B2

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