Benzyl Chloride → HCID 19104990, compound

HRID 1197791Notes

Reaction equation

HRID 1197791 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[CH:10]([CH2:17][C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[C:9]2=[O:24])=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:27](Cl)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[C:10]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([CH2:17][C:18]3[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=3)[C:9]2=[O:24])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 19104983HCID 19104983, compound

Product 1

HCID 19104990HCID 19104990, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1,3-dihydro-1-(4-chlorophenyl)-3-(4-pyridinylmethyl)-2H-pyrrolo[2,3-b]pyridin-2-one (3.0 g, 8.93 mmol) and 20 ml 1N NaOH was treated with enough MeOH to effect solution. The mixture was treated with benzyl chloride (1.24 g, 9.82 mmol) and stirred at room temperature for 24 h. The resulting solid was collected by filtration, washed with water, and dried in vacuo to give the desired product in 87% (3.30 g) yield; mp 182°-185° C.; IR(nujol): 1727 cm-1 (CO); 1H NMR(CDCl3TMS): d 3.29 (dd, 2H, Phe-CH2), 3.4-3.-7 (g, 2H, Pyr-CH2), [6.75 (d, J=8.8, 2H), 6.9 (m, 2H), 7.1 (m, 6H), 7.35 (d, J=8.4, 2H), 7.61 (d, J=7.3, 1H), 8.05 (d, J=6.6, 1H), 8.33 (d, J=6.2, 2H), Ar]; mass spec m/e 426(M+1). Anal calcd for C26H20N3OCl, MW 425.92: C, 73.32; H, 4.73; N,

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-f8b58929a2484456ae4a5535cb749e2a
Source dataset
uspto-grants-1994_01
Patent number
US05278162

Reaction notes

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