HCID 21195131, compound → HCID 21195133, compound

HRID 399149Notes

Reaction equation

HRID 399149 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH:12]=[C:11]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:10]=2)[CH:6]=[CH:5][CH:4]=1)#[N:2].[H][H]>C(O)(=O)C.[Pd]>[NH2:2][CH2:1][C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH:12]=[C:11]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:10]=2)[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 21195131HCID 21195131, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21195133HCID 21195133, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

6-Cyano-4'-(4-methoxyphenyl)-2,2':6',2"-terpyridine (1 mmol) in 33 ml of glacial acetic acid was reduced with hydrogen in the presence of 0.1 g of 10% palladium catalyst on carbon in a Parr apparatus at 40-50 psi and 40°-45° C. for three days. The catalyst was removed by filtration under nitrogen, and the product was purified using a silica gel column by elution with 2.5% ammonium hydroxide/5% methanol/92.5% methylene chloride to yield 0.24 g (65%) of product as a hemi-hydrate. 1H NMR (CDCl3): 1.87 (singlet (s), exchanges with D2O); 3.90 (s, 3H, MeO--); 4.12 (s, 2H, terpyridyl-CH2 --N), 7.08 (doublet (d), 2H, phenyl); 7.35 (multiplet (m), 2H); 7.90 (m and d, 4H); 8.55 (d, 1H); and 8.70 ppm (m, 4H). Calculated: C, 73.19%; H 5.61%; N, 14.84%. Found: C, 72.95%; H, 5.43%; N, 14.61%.

Workup

  1. customThe catalyst was removed by filtration under nitrogen
  2. customthe product was purified
  3. washby elution with 2.5% ammonium hydroxide/5% methanol/92.5% methylene chloride

Sources & evidence

ORD record
ord-05e6f27d944846f9bf087b2bbe756e42
Source dataset
uspto-grants-1998_10
Patent number
US05817774

Reaction notes

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