Tetrahydrofuran → HCID 14255060, compound

HRID 1252490Notes

Reaction equation

HRID 1252490 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=O.O1CCCC1.Cl.Cl.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][CH2:26][CH2:27][NH2:28])[CH:20]=1>O>[NH2:11][C:4]1[CH:3]=[C:2]([Cl:1])[CH:10]=[CH:9][C:5]=1[C:6]([NH:28][CH2:27][CH2:26][CH2:25][C:21]1[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=1)=[O:8]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 666462-Amino-4-chlorobenzoic acidHCID 201401043-(Pyridin-3-yl)propan-1-amine--hydrogen chloride (1/2)

Product 1

HCID 14255060HCID 14255060, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.43 g of 4-chloroanthranilic acid, 3.24 g of N,N'-carbonyldiimidazole and 50 ml of tetrahydrofuran was stirred at 5°-25° C. for 3 hours and 4.18 g of 3-(3-pyridinyl)propylamine dihydrochloride was added. The reaction mixture was stirred at room temperature for 18 hours, heated at reflux temperature for one hour and then with 10 ml of water for 30 minutes. The mixture was concentrated and treated with 100 ml. of methylene chloride and 10 ml of 1N sodium hydroxide. The layers were separated and the organic layer was washed with water, dried over magnesium sulfate and concentrated. The residue was recrystallized from ethyl acetate and the desired product, mp 145°-147° C. was obtained.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 hours
  2. temperatureheated
  3. temperatureat reflux temperature for one hour
  4. concentrationThe mixture was concentrated
  5. additiontreated with 100 ml
  6. customThe layers were separated
  7. washthe organic layer was washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1ccfa358ac404e1ba9f7f6d43e51e98e
Source dataset
uspto-grants-1988_05
Patent number
US04743610

Reaction notes

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