Phthalic Anhydride → HCID 20222715, compound

HRID 979776Notes

Reaction equation

HRID 979776 reaction equation
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][CH2:4][CH2:5][OH:6].[C:13]1(=O)[O:18][C:16](=[O:17])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12>CN(C)C1C=CN=CC=1.O1CCOCC1>[O:17]=[C:16]1[C:15]2[C:14](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13](=[O:18])[N:1]1[CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][CH2:4][CH2:5][OH:6]

Participants

5

Reactant 2

HCID 6811Phthalic AnhydrideHCID 22677686delta-Aminobenzenebutanol

Product 1

HCID 20222715HCID 20222715, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
155 °C

Procedure

Heat a solution of δ-aminobenzenebutanol (7.32 g), phthalic anhydride (6.57 g) and 4-(dimethylamino)pyridine (0.050 g) in dioxane (100 ml) under a nitrogen atmosphere at reflux for one hour. Evaporate the solvent at atmospheric pressure and heat the residue at 155° C. under a nitrogen atmosphere for 21/2 hours. After cooling, dissolve the residue in EtOAc (400 ml). Wash the solution with 10% aqueous citric acid (50 ml) followed by saturated aqueous NaHCO3 (50 ml) and brine (50 ml). Dry the organic layer over Na2SO4, filter and vacuum evaporate the solvent to obtain the title compound.

Workup

  1. temperatureat reflux for one hour
  2. customEvaporate the solvent at atmospheric pressure
  3. temperatureAfter cooling
  4. dissolutiondissolve the residue in EtOAc (400 ml)
  5. washWash the solution with 10% aqueous citric acid (50 ml)
  6. dry with materialDry the organic layer over Na2SO4
  7. filtrationfilter
  8. customvacuum evaporate the solvent

Sources & evidence

ORD record
ord-5795d8fd615547629b6a1f7c848c3ab5
Source dataset
uspto-grants-1987_01
Patent number
US04634689

Reaction notes

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