Dimethylformamide → HCID 85446033, compound

HRID 728192Notes

Reaction equation

HRID 728192 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:18]=[CH:19][C:20]2[N:21]=[C:22]3[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][N:23]3[CH:29]=2)[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.CN(C)[CH:37]=[O:38]>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:18]=[CH:19][C:20]2[N:21]=[C:22]3[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][N:23]3[C:29]=2[CH:37]=[O:38])[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 54191570HCID 54191570, compound

Product 1

HCID 85446033HCID 85446033, compound

Procedure

A solution of 2-[2-(3-benzyloxy-4-nitrophenyl)vinyl]-7-methylimidazo[1,2-a]pyridine (9.00 g) in N,N-dimethylformamide (50 ml), was added dropwise to a solution of phosphorus oxychloride (6.36 ml) in N,N-dimethylformamide (90 ml) at ambient temperature with stirring. After the mixture was stirred for 6 hours, the solvent was evaporated in vacuo. The residue was mixed with water (200 ml) and dichloromethane (300 ml) and made basic with aqueous potassium carbonate. The resulting precipitate was collected, washed with water and recrystallized from a mixture of methanol, chloroform and dioxane to give 2-[2-(3-benzyloxy-4-nitrophenyl)vinyl]-3-formyl-7-methylimidazo[1,2-a]pyridine (5.15 g).

Workup

  1. stirringAfter the mixture was stirred for 6 hours
  2. customthe solvent was evaporated in vacuo
  3. additionThe residue was mixed with water (200 ml) and dichloromethane (300 ml)
  4. customThe resulting precipitate was collected
  5. washwashed with water
  6. customrecrystallized from a mixture of methanol, chloroform and dioxane

Sources & evidence

ORD record
ord-6d3f64696ae742829c2bf5e6db5a77e9
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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