Hydrochloric Acid → 1,2-Benzenedicarbonitrile, 4-nitro-

HRID 1730619

Reaction equation

HRID 1730619 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]([NH2:15])=O)[C:7](=[CH:11][CH:12]=1)[C:8]([NH2:10])=O)([O-:3])=[O:2].P(Cl)(Cl)(Cl)=O.Cl>N1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([C:13]#[N:15])[C:7](=[CH:11][CH:12]=1)[C:8]#[N:10])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 831671,2-Benzenedicarboxamide, 4-nitro-

Product 1

HCID 974431,2-Benzenedicarbonitrile, 4-nitro-Yield 50.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-nitrophthalamide (220 g; 1.05 moles) is suspended in pyridine (840 ml). Into this vigorously stirred suspension, phosphorus oxychloride (220 ml; 2.40 moles) is added at such a rate that the reaction maintains a temperature range of 65°-70° C during the 30-minute addition time. The same temperature is maintained an additional hour by external heating. The resulting mixture is neutralized with 12 N hydrochloric acid (150 ml). The purple solid is collected by filtration and dried. The residue is extracted with ethyl acetate (3 × 700 ml) and the purple extract is decolorized with activated charcoal, washed first with 0.4N sodium hydroxide saturated with sodium chloride (3 × 70 ml) and then with water (4 × 70 ml). Drying and evaporation of the extract leaves 91 g of II as pale yellow crystals; yield, 50%; mp 142-144°; lit. (7-mp 138°-139°; lit. (4) 142°.

Workup

  1. customa temperature range of 65°-70° C
  2. additionduring the 30-minute addition time
  3. temperatureThe same temperature is maintained an additional hour by external heating
  4. filtrationThe purple solid is collected by filtration
  5. customdried
  6. extractionThe residue is extracted with ethyl acetate (3 × 700 ml)
  7. extractionthe purple extract
  8. washwashed first with 0.4N sodium hydroxide saturated with sodium chloride (3 × 70 ml)
  9. customDrying
  10. customevaporation of the extract

Sources & evidence

ORD record
ord-640035ed37c44aee8664d8f25591f018
Source dataset
uspto-grants-1976_11
Patent number
US03993631

Linked notes

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