HCID 10356517, compound → HCID 9994286, compound

HRID 1672306Notes

Reaction equation

HRID 1672306 reaction equation
[N:1]1([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]#[N:22])=[CH:16][CH:15]=2)[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1>N.CO.C1COCC1.[Ni]>[N:1]1([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH2:22])=[CH:16][CH:15]=2)[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 1

HCID 10356517HCID 10356517, compound

Product 1

HCID 9994286HCID 9994286, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1.3 g (4.6 mmol) of (4-imidazo[4,5-c]quinolin-1-yl-phenyl)-acetonitrile (Example 8) and 0.7 g Raney-Ni in 220 ml 10% NH3 in methanol/THF 1:1 are hydrogenated for 6 h at 45° C. and 1.012 bar. The catalyst is filtered off and washed with methanol. The solvent is partially evaporated and diethyl ether is added. The precipitated material is filtered off and discarded. The mother liquor is concentrated to dryness and the title compound is isolated as colorless crystals. MS: 289 (M++1); HPLC: tret=7.57 min (Grad 3).

Workup

  1. filtrationThe catalyst is filtered off
  2. washwashed with methanol
  3. customThe solvent is partially evaporated
  4. additiondiethyl ether is added
  5. filtrationThe precipitated material is filtered off
  6. concentrationThe mother liquor is concentrated to dryness

Sources & evidence

ORD record
ord-04a78cf5870d41ec8dea1e97f3bbbffd
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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