HCID 11044975, compound → HCID 18763022, compound

HRID 431072Notes

Reaction equation

HRID 431072 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][C:19]([N+:21]([O-])=O)=[CH:20][C:13]=3[N:12]=2)=[CH:5][CH:4]=1)#[N:2]>C1COCC1.CO.[Pd]>[NH2:21][C:19]1[CH:18]=[CH:17][C:14]2[N:15]([CH3:16])[C:11]([CH2:10][CH2:9][C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)=[N:12][C:13]=2[CH:20]=1

Participants

5

Reactant 1

HCID 11044975HCID 11044975, compound

Product 1

HCID 18763022HCID 18763022, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-[2-(4-Cyanophenyl)-ethyl]-1-methyl-5-nitro-benzimidazole (5.5 g, 18 mmol) in 150 mL THF and 75 mL methanol is hydrogenated in the presence of 1.0 g of 5% Pd/C at ambient temperature under normal pressure. The catalyst is filtered off, the filtrate is evaporated, not quite to dryness, diluted with 100 mL of acetonitrile and evaporated down to a residual volume of 30 mL. The crystal slurry is cooled and filtered. The crystals are washed with cold acetonitrile and ether.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated, not quite to dryness
  3. additiondiluted with 100 mL of acetonitrile
  4. customevaporated down to a residual volume of 30 mL
  5. temperatureThe crystal slurry is cooled
  6. filtrationfiltered
  7. washThe crystals are washed with cold acetonitrile and ether

Sources & evidence

ORD record
ord-07278b3a00d940808994d4c47f641c0e
Source dataset
uspto-grants-2003_12
Patent number
US06656956B2

Reaction notes

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