Ammonia → 2-(4-Chlorophenyl)-3-(2-oxo-1-pyrrolidinylmethyl)-6-methylimidazo[1,2-a]pyridine

HRID 1906148Notes

Reaction equation

HRID 1906148 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]3[CH:17]=2)=[CH:4][CH:3]=1.O[CH2:19][N:20]1[CH2:24][CH2:23][CH2:22][C:21]1=[O:25].S(=O)(=O)(O)O.N>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]3[C:17]=2[CH2:19][N:20]2[CH2:24][CH2:23][CH2:22][C:21]2=[O:25])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 849112-Pyrrolidinone, 1-(hydroxymethyl)-HCID 7359112-(4-Chlorophenyl)-6-methylimidazo[1,2-a]pyridine

Product 1

HCID 135896012-(4-Chlorophenyl)-3-(2-oxo-1-pyrrolidinylmethyl)-6-methylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An intimate mixture is prepared of 4.8 g (0.02 mol) of 2-(4-chlorophenyl)-6-methylimidazo[1,2-a]pyridine and 2.53 g (0.022 mol) of N-hydroxymethyl-2-pyrrolidinone, and this is then introduced into 20 ml of concentrated sulphuric acid. The solution is stirred for one day at room temperature, then poured into 800 ml of water, and 55 ml of ammonia solution are added. The lactam is extracted with methylene chloride, the organic phase is washed, dried and evaporated, and the residue is purified by chromatography, eluting with a 70:30 ethyl acetate, toluene mixture. The white solid obtained melts at 186°-187.5° C.

Workup

  1. additionare added
  2. extractionThe lactam is extracted with methylene chloride
  3. washthe organic phase is washed
  4. customdried
  5. customevaporated
  6. customthe residue is purified by chromatography
  7. washeluting with a 70:30 ethyl acetate, toluene mixture
  8. customThe white solid obtained melts at 186°-187.5° C.

Sources & evidence

ORD record
ord-d734378739904929b8c1d367de515346
Source dataset
uspto-grants-1987_03
Patent number
US04650796

Reaction notes

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