Ethanol → HCID 67609537, compound

HRID 925291Notes

Reaction equation

HRID 925291 reaction equation
[CH2:1]([N:3]([CH2:21][CH3:22])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([C:13]#[N:14])[N:10]=[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:8]=1)[CH3:2].C([O-])=O.[NH4+].C(O)C>O.[OH-].[Pd+2].[OH-].[Pd]>[NH2:14][CH2:13][C:11]1[N:10]=[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:8]=[C:7]([O:6][CH2:5][CH2:4][N:3]([CH2:21][CH3:22])[CH2:1][CH3:2])[CH:12]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 2723923Ammonium formateHCID 67609763HCID 67609763, compound

Product 1

HCID 67609537HCID 67609537, compound

Reagents, catalysts & solvents 2

HCID 86707187HCID 86707187, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
27 °C

Procedure

A mixture of 4-(2-Diethylamino-ethoxy)-[2,2′]bipyridinyl-6-carbonitrile (1.4 g, 5.22 mmol), Palladium hydroxide-Pd 20%-50% in water (2.25 g, excess), ammonium formate (1.65 g, excess) and ethanol (66 mL) was stirred at 27° C. for 2 hours. The reaction was then filtered thorough celite, washed with methanol (200 mL) and dichloromethane (200 mL) and the organic phase evaporated to dryness affording [2-(6-aminomethyl-[2,2′]bipyridinyl-4-yloxy)-ethyl]diethylamine as an orange oil (1.03 g, 30%, in a ratio 1 to 1 product vs. byproduct).

Workup

  1. filtrationThe reaction was then filtered thorough celite
  2. washwashed with methanol (200 mL) and dichloromethane (200 mL)
  3. customthe organic phase evaporated to dryness

Sources & evidence

ORD record
ord-a280255525fc40b8acdfb9c28f94c348
Source dataset
uspto-grants-2016_03
Patent number
US09284296B2

Reaction notes

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