Ammonia → HCID 19760136, compound

HRID 1586934Notes

Reaction equation

HRID 1586934 reaction equation
N.[Na].[CH3:3][C:4]1[CH:9]=[C:8]([CH3:10])[N:7]=[C:6]([C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[N:12]=2)[CH:5]=1.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>[N+]([O-])([O-])=O.[Fe+3].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.C(Cl)(Cl)Cl.C(O)C.O>[C:20]1([CH2:19][CH2:3][C:4]2[CH:9]=[C:8]([CH3:10])[N:7]=[C:6]([C:11]3[CH:16]=[C:15]([CH2:17][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:14]=[C:13]([CH3:18])[N:12]=3)[CH:5]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

9

Reactant 4

HCID 222AmmoniaHCID 7498Benzyl BromideHCID 5360545Sodium2×HCID 141486094,4',6,6'-Tetramethyl-2,2'-bipyridine

Product 1

HCID 19760136HCID 19760136, compound

Reagents, catalysts & solvents 4

HCID 25251Ferric nitrateCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
-50 °C

Procedure

To liquid ammonia (20 ml) at -50° C. enough sodium was added to maintain a blue colored solution. Iron (III) nitrate (20 mg) was added and then sodium (0.19 g, 0.008 gr.atom). After 45 minutes 4,4',6,6'-tetramethyl-2,2'-bipyridine (26) (1.06 g, 5.00 mmoles) was added in small portions and the mixture was stirred for 1.5 hours at -50° C. Benzyl bromide (1.88 g, 11.0 mmoles) was added at -50° C. during 2 hours. The mixture was allowed to warm and water (50 ml), ethanol (20 ml) and chloroform (30 ml) was added. The organic phase was extracted with saturated ammonium sulfate solution, dried with magnesium sulfate and evaporated. By addition of ethyl acetate some pure compound was precipitated. The rest was purified by means of flash chromatography (silica, 0-6% methanol/dichloromethane).

Workup

  1. temperatureto maintain a blue colored solution
  2. temperatureto warm
  3. extractionThe organic phase was extracted with saturated ammonium sulfate solution
  4. dry with materialdried with magnesium sulfate
  5. customevaporated
  6. additionBy addition of ethyl acetate some pure compound
  7. customwas precipitated
  8. customThe rest was purified by means of flash chromatography (silica, 0-6% methanol/dichloromethane)

Sources & evidence

ORD record
ord-3c3a9b6599ca4756abac75e7efde9619
Source dataset
uspto-grants-1993_06
Patent number
US05216134

Reaction notes

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