2,2'-Dipyridylamine → 3,3-Bis-(2-pyridyl)propionaldehyde dimethyl acetal

HRID 2181638Notes

Reaction equation

HRID 2181638 reaction equation
N1C=CC=CC=1NC1C=CC=CN=1.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)[C:21]#N.[CH3:29][O:30][CH:31]([O:34][CH3:35])CBr>>[CH3:29][O:30][CH:31]([O:34][CH3:35])[CH2:21][CH:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=1

Participants

4

Reactant 3

HCID 145472,2'-DipyridylamineHCID 816722-Bromo-1,1-dimethoxyethaneHCID 140060572,2-Bis-(2-pyridyl)acetonitrile

Product 1

HCID 224820933,3-Bis-(2-pyridyl)propionaldehyde dimethyl acetalYield 77%

Procedure

This product was prepared as described above, (in Example 5), with the exception that bis-(2-pyridyl)amine was replaced by bis-(2-pyridyl)methane (prepared as described in Heterocycles 1995, 40, 757-776) and substituting 1-(2-chloroethyl)-4-(2-methoxyphenyl)piperazine with 2-bromoacetaldehyde dimethyl acetal. After 12.5 h at reflux the reaction mixture was worked-up as described above. The crude residue was purified by flash chromatography (ethyl acetate-petroleum ether-2.2 N methanolic ammonia 6:4:0.6) affording the title product (77%).

Workup

  1. customThis product was prepared
  2. temperatureAfter 12.5 h at reflux the reaction mixture
  3. customThe crude residue was purified by flash chromatography (ethyl acetate-petroleum ether-2.2 N methanolic ammonia 6:4:0.6)

Sources & evidence

ORD record
ord-1f4544878366435683fb0356b199f427
Source dataset
uspto-grants-2005_05
Patent number
US06894052B1

Reaction notes

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