Pyridine → 4-nitro-N-(pyridin-4-ylmethyl)benzamide

HRID 1951587Notes

Reaction equation

HRID 1951587 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.N1C=CC=CC=1.[N+:15]([C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1)([O-:17])=[O:16]>ClCCl>[N+:15]([C:18]1[CH:19]=[CH:20][C:21]([C:22]([NH:1][CH2:2][C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)=[O:23])=[CH:25][CH:26]=1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 85024-Nitrobenzoyl chlorideHCID 773174-Pyridinemethanamine

Product 1

HCID 21648024-nitro-N-(pyridin-4-ylmethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

to a solution of 4-(aminomethyl)pyridine (12.9 ml, 127 mmol) and pyridine (51.4 ml, 636 mmol) in 150 mL dichloromethane cooled by an ice bath was added 4-nitrobenzoyl chloride (24.8 g, 133 mmol) all at once, generating a dark red reaction solution. LC-MS at 5 minutes indicated reaction complete and the desired product predominated. The reaction was stirred at room temperature overnight then the solid collected by filtration. LC-MS indicated that the filtrate was desired product. The solid was washed with 5% aqueous sodium hydroxide solution until aqueous layer was alkaline then the solid collected by filtration. The solid was dried overnight in a vacuum dessicator over P2O5 (28.4 g, 87%). ESI+ m/z=258.1 [MH]+.

Workup

  1. customreaction complete

Sources & evidence

ORD record
ord-7d16e331d56344e18d9170b04bd2cbd2
Source dataset
uspto-grants-2013_03
Patent number
US08404722B2

Reaction notes

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