Pyridine → HCID 19864466, compound

HRID 1199968Notes

Reaction equation

HRID 1199968 reaction equation
C1C=C[NH+]=CC=1.Br[Br-]Br.[O:10]=[C:11]1[NH:16][N:15]=[C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH2:28][CH2:27][C:26](=[O:29])[NH:25][N:24]=3)=[CH:19][CH:18]=2)[CH2:13][CH2:12]1.N1C=CC=CC=1>C(O)(=O)C>[O:29]=[C:26]1[NH:25][N:24]=[C:23]([C:20]2[CH:21]=[CH:22][C:17]([C:14]3[CH:13]=[CH:12][C:11](=[O:10])[NH:16][N:15]=3)=[CH:18][CH:19]=2)[CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 1049PyridineHCID 19864467HCID 19864467, compound

Product 1

HCID 19864466HCID 19864466, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of pyridinium bromide perbromide (0.6 g) in hot acetic acid (50 ml) was added dropwise over 10 minutes to a refluxing mixture of 1,4-bis(6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)benzene (0.5 g) and pyridine (0.3 ml) in glacial acetic acid (100 ml). After addition the clear brown solution was stirred under reflux for 3 hours and was cooled and filtered. The filtrate was concentrated to small volume (ca 10 ml) and was treated with distilled water (100 ml) to yield a brown solid which was collected, washed with ethanol and ether and then dried. The crude material is recrystallised from acetic acid to afford the title compound, m.p. greater than 250° C., H NMR: δ (DMSOd6); 2.45 (2H, t), 2.95 (2H, t), 7.00 (1H, d), 7.88 (4H, m), 8.08 (1H, d) and 10.88 (1H, s).

Workup

  1. additionAfter addition the clear brown solution
  2. temperatureunder reflux for 3 hours
  3. temperaturewas cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated to small volume (ca 10 ml)
  6. additionwas treated with distilled water (100 ml)
  7. customto yield a brown solid which
  8. customwas collected
  9. washwashed with ethanol and ether
  10. customdried
  11. customThe crude material is recrystallised from acetic acid

Sources & evidence

ORD record
ord-cc076d0879f6402a8eb7ec17addc9302
Source dataset
uspto-grants-1990_02
Patent number
US04904664

Reaction notes

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