Hydrazine → HCID 21074529, compound

HRID 1373680Notes

Reaction equation

HRID 1373680 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH3:18])[NH:11][C:12]=2[CH2:13]CCCN)=[CH:4][CH:3]=1.ClC1[N:25]=[CH:24][C:23](C2N=C(C)NC=2CCCCN2C(=O)C3C(=CC=CC=3)C2=O)=[CH:22]C=1.NN>C(O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:18][CH2:22][CH2:23][CH2:24][NH2:25])[NH:11][C:12]=2[CH3:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 86599606HCID 86599606, compoundHCID 86599607HCID 86599607, compound

Product 1

HCID 21074529HCID 21074529, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

4-[4-(6-chloro(3-pyridyl))-2-methylimidazolyl]butylamine. To a solution of 2-{4-[4-(6-chloro(3-pyridyl))-2-methylimidazolyl]butyl}-isoindole-1,3-dione (1.0 g, 2.54 mmoles) in ethanol (25 ml) was added hydrazine (0.24 ml, 7.6 mmoles). After heating the reaction mixture in a 80° C. oil bath for 3 hours, the solution was cooled, filtered, and concentrated. The resulting oil was taken up in dichloromethane (100 ml) and was washed with 1M NaOH (15 ml). The aqueous layer was extracted further with dichloromethane (2×100 ml), the combined organics were dried over MgSO4, filtered, and concentrated yielding 4-[4-(6-chloro(3-pyridyl))-5-methylimidazolyl]butylamine (500 mg, 75%). MH+(265).

Workup

  1. temperaturethe solution was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. washwas washed with 1M NaOH (15 ml)
  5. extractionThe aqueous layer was extracted further with dichloromethane (2×100 ml)
  6. dry with materialthe combined organics were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4d4d8b5f92764cc3afb4c7a0e8ed06ca
Source dataset
uspto-grants-2007_01
Patent number
US07163924B2

Reaction notes

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