Phosphorus oxychloride → HCID 20446658, compound

HRID 2417818Notes

Reaction equation

HRID 2417818 reaction equation
[CH:1]([NH:3][CH2:4][C:5]1[CH:10]=[C:9]([CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:8]=[CH:7][N:6]=1)=O.P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH3:17][O:16][C:14]([CH2:13][CH2:12][CH2:11][C:9]1[CH:8]=[CH:7][N:6]2[CH:1]=[N:3][CH:4]=[C:5]2[CH:10]=1)=[O:15]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 20446686HCID 20446686, compound

Product 1

HCID 20446658HCID 20446658, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(N-formylaminomethyl)-4-(3-methoxycarbonylpropyl)pyridine (33 mg) is dissolved in 1 ml of toluene and heated at 90° with phosphorus oxychloride (44 mg) for 18 hours under nitrogen. The solvent is evaporated and the residue is suspended in methylene chloride, cooled to 0° and made basic with saturated ammonium hydroxide solution. The aqueous phase is extracted with methylene chloride (4×15 ml) which is dried over sodium sulfate and evaporated to yield 7-(3-methoxycarbonylpropyl)imidazo[1,5-a]pyridine as an oil, after purification by preparative thin layer chromatography (silica gel, 3:1 ethyl acetate-methanol); NMR (CDCl3) 3.70 (s, 3H); 6.45 (q, 1H), 7.2 (s, 1H), 7.32 (s, 1H), 7.90 (d, 1H); 8.08 (s, 1H); IR (CH2Cl2) 1730 cm-1.

Workup

  1. customThe solvent is evaporated
  2. temperaturecooled to 0°
  3. extractionThe aqueous phase is extracted with methylene chloride (4×15 ml) which
  4. dry with materialis dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-c10421afd6324664a436d37aece4a784
Source dataset
uspto-grants-1984_09
Patent number
US04470986

Reaction notes

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