Hydrochloric Acid → HCID 54191570, compound

HRID 728105Notes

Reaction equation

HRID 728105 reaction equation
[Cl-].Cl[CH2:3][C:4](=O)[CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[NH2:26][C:27]1[CH:32]=[C:31]([CH3:33])[CH:30]=[CH:29][N:28]=1.[CH2:34]([O:41][C:42]1[CH:43]=[C:44]([CH:47]=[CH:48][C:49]=1[N+:50]([O-:52])=[O:51])[CH:45]=O)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(=O)([O-])[O-].[K+].[K+].Cl>C(#N)C.O>[CH2:34]([O:41][C:42]1[CH:43]=[C:44]([CH:45]=[CH:5][C:4]2[N:26]=[C:27]3[CH:32]=[C:31]([CH3:33])[CH:30]=[CH:29][N:28]3[CH:3]=2)[CH:47]=[CH:48][C:49]=1[N+:50]([O-:52])=[O:51])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 15332-Amino-4-methylpyridineHCID 11430Potassium Carbonate2×HCID 27736283-Chloro-2-oxopropyl triphenylphosphonium chlorideHCID 12111719HCID 12111719, compound

Product 1

HCID 54191570HCID 54191570, compoundYield 45.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of (chloroacetonyl)triphenylphosphonium chloride (190.7 g) and 2-amino-4-methylpyridine (158.9 g) in acetonitrile (1.3 l) was stirred under reflux for 5.5 hours. To the reaction mixture were added water (400 ml) and 3-benzyloxy-4-nitrobenzaldehyde (63.0 g) under ice-cooling. The mixture was adjusted to pH 9.5 with potassium carbonate and stirred for 2.5 hours at ambient temperature under keeping the pH 9.5 to 10.0 with 20% aqueous potassium carbonate. The reaction mixture was adjusted to pH 2.0 with conc. hydrochloric acid and the precipitate was collected by filtration. To a mixture of ethyl acetate, tetrahydrofuran and water was added the above obtained precipitate and the resultant mixture was adjusted to pH 7.0 with 20% aqueous potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo to give 2-[2-(3-benzyloxy-4-nitrophenyl)vinyl]-7-methylimidazo[1,2-a]pyridine (43.14 g).

Workup

  1. temperatureunder reflux for 5.5 hours
  2. temperaturecooling
  3. stirringstirred for 2.5 hours at ambient temperature
  4. filtrationthe precipitate was collected by filtration
  5. additionTo a mixture of ethyl acetate, tetrahydrofuran and water
  6. additionwas added the above obtained precipitate
  7. washThe separated organic layer was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-87938e24a82a4465a7dfa21c333e36c3
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

Loading…