Water → 1-(N-benzyl-N-phenylamino)naphthalene

HRID 1608713Notes

Reaction equation

HRID 1608713 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]1([NH:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[K+].O>CN1CCCC1=O>[CH2:1]([N:15]([C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7013Phenyl-1-naphthylamineHCID 7498Benzyl BromideHCID 14797Potassium Hydroxide

Product 1

HCID 157015421-(N-benzyl-N-phenylamino)naphthaleneYield 65%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Benzyl bromide (0.15M) was added to a stirred mixture of 1-phenylaminonaphthalene (0.1M) and KOH (0.15M) in N-methyl pyrrolidone (70 cm3) at 120° C. After 2 hours further stirring the mixture was poured in to water, the precipitate filtered off, washed and re-crystallised from methanol to give 20 g (65% yield) of a white solid mp 120°-123° C.

Workup

  1. filtrationthe precipitate filtered off
  2. washwashed
  3. customre-crystallised from methanol

Sources & evidence

ORD record
ord-08b88dc7a10848259c4a9d3cfbdab350
Source dataset
uspto-grants-1995_03
Patent number
US05395969

Reaction notes

Loading…