O-Xylene → N-Methylenepyrrolidonyl-2-Cyclopentoxyaniline

HRID 262014

Reaction equation

HRID 262014 reaction equation
[CH:1]1([O:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[NH2:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([N:16]1[CH2:20][CH2:19][CH2:18][C:17]1=[O:21])O.[C:22]1(C)C(C)=CC=CC=1>O>[CH2:22]=[N:9][C:8]1[CH:10]=[CH:11][CH:12]=[C:13]([N:16]2[CH2:20][CH2:19][CH2:18][C:17]2=[O:21])[C:7]=1[O:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 849112-Pyrrolidinone, 1-(hydroxymethyl)-HCID 64853982-(Cyclopentyloxy)aniline

Product 1

HCID 70609772N-Methylenepyrrolidonyl-2-CyclopentoxyanilineYield 51.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Cyclopentoxyaniline (10.0 g, 0.057 mole), N-methylolpyrrolidone (9.75 g, 0.85 mole) and xylene (25 cc) were refluxed under azeotropic conditions with the removal of 1.5 cc of water. The xylene was removed by rotary evaporation and the product was crystallized from 100 cc of hexane to yield 8.0 g (51.6%) of product, m.p. 87°-87.5° C.

Workup

  1. customThe xylene was removed by rotary evaporation
  2. customthe product was crystallized from 100 cc of hexane

Sources & evidence

ORD record
ord-620428e63c7243ba8d19feeb5620722f
Source dataset
uspto-grants-1979_05
Patent number
US04153446

Linked notes

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