Water → 2-bromo-4-(4-pyridinylmethyl)Benzenamine

HRID 2209462

반응식

HRID 2209462 반응식
[Br:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[CH:22]=[CH:21][C:13]([CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:12][CH:11]=1.O>CN(C)C=O.[Al]>[NH2:9][C:10]1[CH:22]=[CH:21][C:13]([CH2:14][C:15]2[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=2)=[CH:12][C:11]=1[Br:1]

참가 물질

6

반응물 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 3071584-[(Pyridin-4-yl)methyl]aniline

생성물 1

HCID 218656452-bromo-4-(4-pyridinylmethyl)Benzenamine수율 77.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 5359268Aluminum용매

실험 절차

A solution of N-bromosuccinimide (1.4 gm) in 10 mL dimethylformamide was added in a dropwise manner to a solution of 4-(4-aminobenzyl)pyridine (1.5 gm) in 10 mL of dimethylformamide. The reaction flask was wrapped in aluminum foil to prevent exposure of the reagents to light. The reaction mixture was stirred at room temperature for 3 hours. The progress of the reaction was monitored by thin-layer chromatography. When the reaction was completed, the reaction mixture was combined with 100 mL of H2O with stirring. A reddish brown precipitate was formed, filtered out of solution, washed with H2O, and air dried. The solid was dissolved in ethyl acetate, back washed with saturated NaCl, dried over MgSO4 and triturated with ethyl ether. The solid was filtered from the solution and air dried yielding 1.6 gm of 4-(4-amino-3-bromobenzyl)pyridine as reddish/tan crystals.

후처리

  1. stirringwith stirring
  2. customA reddish brown precipitate was formed
  3. filtrationfiltered out of solution
  4. washwashed with H2O, and air
  5. customdried
  6. dissolutionThe solid was dissolved in ethyl acetate
  7. washback washed with saturated NaCl
  8. dry with materialdried over MgSO4
  9. customtriturated with ethyl ether
  10. filtrationThe solid was filtered from the solution and air
  11. customdried

출처 및 근거

ORD 기록
ord-29c5a1d3b02141a78591019cf7cdb68e
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05455252

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