HCID 11722607, compound → HCID 10403048, compound

HRID 1672318Notes

Reaction equation

HRID 1672318 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]=[CH:13][N:14]([C:15]4[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=4)[C:18]#[N:19])[C:5]=3[C:4]=2[CH:3]=1>CO.N.[Ni]>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]=[CH:13][N:14]([C:15]4[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=4)[CH2:18][NH2:19])[C:5]=3[C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 11722607HCID 11722607, compound

Product 1

HCID 10403048HCID 10403048, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

300 mg (0.98 mmol) of 3-(8-chloro-imidazo[4,5-c]quinolin-1-yl)-benzonitrile (Example 35) in 20 ml methanol/NH3 10% and 250 mg Raney-Ni are hydrogenated at rt for 5 h. The reaction solution is filtered on Hyflo® Super Cel diatomaceous earth and is evaporated to dryness. The title compound is crystallized from ethyl acetate-hexane to yield a grey powder. Drying is done for 16 h at 60° C. (high-vacuum). mp: 148-149° C.; MS: 309 (M++1); HPLC: tret=8.87 min (Grad 3).

Workup

  1. filtrationThe reaction solution is filtered on Hyflo® Super Cel diatomaceous earth
  2. customis evaporated to dryness
  3. customThe title compound is crystallized from ethyl acetate-hexane
  4. customto yield a grey powder
  5. customDrying
  6. customtret=8.87 min (Grad 3)

Sources & evidence

ORD record
ord-0fd005f996b74245842c3d689ac39af2
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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