HCID 67333492, compound → HCID 68437142, compound

HRID 1170179Notes

Reaction equation

HRID 1170179 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH2:7][NH:8][C:9]2[CH:18]=[CH:17][C:16]3[C:15]([C:19]#[N:20])=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=2)=[CH:4][CH:3]=1>CO.N>[NH2:20][CH2:19][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:16]=1[CH:17]=[CH:18][C:9]([NH:8][CH2:7][C:5]1[O:6][C:2]([CH3:1])=[CH:3][CH:4]=1)=[N:10]2

Participants

3

Reactant 1

HCID 67333492HCID 67333492, compound

Product 1

HCID 68437142HCID 68437142, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 21705897Ammonia methanolSolvent

Procedure

Hydrogenation of 2-[(5-methyl-furan-2-ylmethyl)-amino]-quinoline-5-carbonitrile (200 mg, 0.76 mmol) dissolved in 7N MeOH—NH3 for 23 h at room temperature yielded after removal of the catalyst by filtration and evaporation a yellow oil which was further purified by column chromatography (dichloromethane/MeOH/NH4OH 15:1:0.1) on silica gel to yield (5-aminomethyl-quinolin-2-yl)-(5-methyl-furan-2-ylmethyl)-amine as light yellow oil (198 mg, 98%).

Workup

  1. customyielded
  2. customafter removal of the catalyst
  3. filtrationby filtration and evaporation a yellow oil which
  4. customwas further purified by column chromatography (dichloromethane/MeOH/NH4OH 15:1:0.1) on silica gel

Sources & evidence

ORD record
ord-d1a77b038816484bbad5b7a1f508f33c
Source dataset
uspto-grants-2010_11
Patent number
US07825253B2

Reaction notes

Loading…