Hydrochloric Acid → HCID 10339105, compound

HRID 1672350Notes

Reaction equation

HRID 1672350 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]=[C:13]([CH2:22][C:23]([NH:25]O)=[NH:24])[N:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[Cl:21])[C:5]=3[C:4]=2[CH:3]=1.Cl>O.[Ni]>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]=[C:13]([CH2:22][C:23]([NH2:25])=[NH:24])[N:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[Cl:21])[C:5]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178510883HCID 178510883, compound

Product 1

HCID 10339105HCID 10339105, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

352 mg (0.91 mmol) of 2-[8-chloro-1-(2-chloro-phenyl)-1H-imidazo[4,5-c]quinolin-2-yl]-N-hydroxy-acetamidine (Example 87), 0.91 ml 1N HCl, in 7.1 ml water are hydrogenated at rt (tlc-control) in the presence of ca. 190 mg Raney-Ni. The catalyst is filtered off and washed with methanol. The solvents are evaporated, the residue is dissolved in CH2Cl2-water-methanol. The two phases are separated and evaporated. From the water phase, a yellow oil separates. The oil is dissolved in hot methanol and diethyl ether is added. On stirring at 0-5° C., a solid separates. The solid, which is the title compound, is filtered off and dried for 6 h at 50° C. MS: 370 (M++1); HPLC: tret=7.38 min (Grad 1).

Workup

  1. customare hydrogenated at rt
  2. filtrationThe catalyst is filtered off
  3. washwashed with methanol
  4. customThe solvents are evaporated
  5. dissolutionthe residue is dissolved in CH2Cl2-water-methanol
  6. customThe two phases are separated
  7. customevaporated
  8. dissolutionThe oil is dissolved in hot methanol
  9. additiondiethyl ether is added
  10. filtrationis filtered off
  11. customdried for 6 h at 50° C
  12. customtret=7.38 min (Grad 1)

Sources & evidence

ORD record
ord-e5f96c13c2dd4cbba14d350b05a90ba3
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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