3,4,5,6-Tetrahydrophthalic anhydride → HCID 20486113, compound

HRID 1995835Notes

Reaction equation

HRID 1995835 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2[CH2:7][CH2:8][CH2:9][CH2:10][C:2]1=2.[NH2:12][C:13]1[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[N:17][CH:18]=1>C(O)(=O)C>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][CH2:20][O:19][C:16]2[CH:15]=[CH:14][C:13]([N:12]3[C:1](=[O:11])[C:2]4[CH2:10][CH2:9][CH2:8][CH2:7][C:3]=4[C:4]3=[O:6])=[CH:18][N:17]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 204860856-[2-(4-Chlorophenyl)ethoxy]pyridin-3-amine

Product 1

HCID 20486113HCID 20486113, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3,4,5,6-tetrahydrophthalic anhydride (0.4 g), 5-amino-2-(4-chlorophenethoxy)pyridine (0.6 g) and acetic acid (20 ml) is heated to reflux. After about 1.5 hours, the reaction is cooled and concentrated to about one-half volume. On standing, a crystalline solid precipitates which is collected by filtration and washed with 10% ethyl acetate/hexane to yield N-[2-(4-chlorophenethoxy)-5-pyridyl]-3,4,5,6-tetrahydrophthalimide.

Workup

  1. temperatureis heated to reflux
  2. temperaturethe reaction is cooled
  3. concentrationconcentrated to about one-half volume
  4. customa crystalline solid precipitates which
  5. filtrationis collected by filtration
  6. washwashed with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-dde3b247bfd249cb84fa4ae6bfe2ddf7
Source dataset
uspto-grants-1983_09
Patent number
US04406689

Reaction notes

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