Sodium Hydroxide → [2-[[3-(Dimethylamino)propyl](3-nitro-2-pyridinyl)amino]phenyl]phenylmethanone

HRID 463022

Reaction equation

HRID 463022 reaction equation
Cl.[N+:2]([C:5]1[C:6]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:19])=[N:7][CH:8]=[CH:9][CH:10]=1)([O-:4])=[O:3].[CH3:26][N:27]([CH3:32])[CH2:28][CH2:29][CH2:30]Cl.[Cl-].C([NH+](C(=O)CCCCCCC)C(=O)CCCCCCC)(=O)CCCCCCC.[OH-].[Na+]>O.C(Cl)Cl>[CH3:26][N:27]([CH3:32])[CH2:28][CH2:29][CH2:30][N:11]([C:6]1[C:5]([N+:2]([O-:4])=[O:3])=[CH:10][CH:9]=[CH:8][N:7]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 19098081Tricaprylylammonium chlorideHCID 70409212[2-[(3-Nitro-2-pyridinyl)amino]phenyl]phenylmethanone hydrochloride

Product 1

HCID 54525496[2-[[3-(Dimethylamino)propyl](3-nitro-2-pyridinyl)amino]phenyl]phenylmethanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.6 g (0.01 mole) of [2-[(3-nitro-2-pyridinyl)amino]phenyl]phenylmethanone hydrochloride, 4.7 g (0.03 mole) of 3-dimethylaminopropyl chloride, 0.1 g of tricaprylyl ammonium chloride, 16 g (0.20 moles) of 50% aqueous sodium hydroxide, 25 ml methylene chloride, and 5 ml water was refluxed for 27 hrs. Chemical ionization mass spectroscopy analysis indicated the product was mainly the title compound. The mixture was cooled and diluted with methylenechloride-water mixture. The aqueous layer was extracted twice with methylene chloride. The combined methylene chloride layers were washed with aqueous sodium chloride solution, dried, treated with charcoal, filtered and evaporated to give 3.3 g black material (81.5%) which was predominantly the title compound as indicated by thin-layer chromatography and chemical ionization mass spectroscopy analysis of the chromatographed material, i.e. m/e=405.

Workup

  1. temperaturewas refluxed for 27 hrs

Sources & evidence

ORD record
ord-00f0e561a7ca4747a968f651ed0a8237
Source dataset
uspto-grants-1985_05
Patent number
US04518603

Linked notes

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