1,3-Propanediamine → HCID 14397366, compound

HRID 1906546Notes

Reaction equation

HRID 1906546 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[NH2:12][CH2:13][CH2:14][CH2:15][NH2:16].N1C=CC=CC=1>CO>[NH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 4281,3-PropanediamineHCID 1049PyridineHCID 896482-Chloro-3-methyl-5-nitropyridine

Product 1

HCID 14397366HCID 14397366, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Chloro-3-methyl-5-nitropyridine (15.5 g), 1,3-diaminopropane (30 ml) and pyridine (10 ml) were stirred together and, after the initial exotherm had subsided, the mixture was heated under reflux for 1.5 hr. On cooling the mixture was treated with methanol and the bulk of crystalline bi-product filtered off. The solution was stripped, the residue taken up in water and the pH adjusted to 6.5 with hydrochloric acid. After filtering through `Hyflo` the solution was extracted with chloroform. The pH was raised to 14, (NaOH) and extracted with ether. After drying (K2CO3), the ether extracts were stripped to give a yellow solid which was triturated with ether/pentane to give 2-(3-aminopropylamino)-3-methyl-5-nitropyridine, (12.9 g; 68%) m.p. 93°-95° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hr
  3. temperatureOn cooling the mixture
  4. filtrationthe bulk of crystalline bi-product filtered off
  5. filtrationAfter filtering through `Hyflo` the solution
  6. extractionwas extracted with chloroform
  7. temperatureThe pH was raised to 14, (NaOH)
  8. extractionextracted with ether
  9. dry with materialAfter drying (K2CO3)
  10. customto give a yellow solid which
  11. customwas triturated with ether/pentane

Sources & evidence

ORD record
ord-23b792b8307b49c7a13ad525289ac58f
Source dataset
uspto-grants-1987_03
Patent number
US04652650

Reaction notes

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