Hydrazine → HCID 178510962, compound

HRID 2055145Notes

Reaction equation

HRID 2055145 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])[NH:11][CH:12]=2)=[CH:4][CH:3]=1.[Cl:18]C1C=CN=CC=1C1N=CN(CN2C(=O)C3C(=CC=CC=3)C2=O)C=1.NN>C(O)C>[Cl:18][C:4]1[CH:3]=[CH:2][N:7]=[CH:6][C:5]=1[C:8]1[N:9]=[C:10]([CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])[NH:11][CH:12]=1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 21074543HCID 21074543, compoundHCID 178510961HCID 178510961, compound

Product 1

HCID 178510962HCID 178510962, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

4-[4-(6-chloro-3-pyridyl)imidazolyl]butylamine. To a solution of 2-[4-(4-chloro-pyridin-3-yl)-imidazol-1-ylmethyl]-isoindole-1,3-dione (2.82 g, 7.42 mmoles) in ethanol (75 ml) was added hydrazine (0.58 ml, 18.6 mmoles). After heating the reaction mixture in a 65° C. oil bath for 15 hours, the solution was cooled, filtered, and concentrated. The resulting oil was taken up in dichloromethane (200 ml) and was washed with 1M NaOH (250 ml). The aqueous layer was extracted further with dichloromethane (2×200 ml), the combined organics were dried over MgSO4, filtered, and concentrated yielding 4-[4-(4-chloro-3-pyridyl)imidazolyl]butylamine (1.74 g, 94%). MH+(251)

Workup

  1. temperaturethe solution was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. washwas washed with 1M NaOH (250 ml)
  5. extractionThe aqueous layer was extracted further with dichloromethane (2×200 ml)
  6. dry with materialthe combined organics were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-310d43967c3b4090ad4b397e9abad86f
Source dataset
uspto-grants-2008_02
Patent number
US07332476B2

Reaction notes

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