Phosphorus oxychloride → HCID 178478309, compound

HRID 1292478Notes

Reaction equation

HRID 1292478 reaction equation
[NH:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[C:5](O)[C:4]=2[N:3]=[CH:2]1.P(Cl)(Cl)([Cl:17])=O.C(=O)(O)[O-].[Na+]>>[Cl:17][C:5]1[C:4]2[N:3]=[CH:2][NH:1][C:13]=2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:6]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178517113HCID 178517113, compound

Product 1

HCID 178478309HCID 178478309, compound

Procedure

A mixture of 500 mg of 1H-imidazo[4,5-c]quinolin-4-ol and about 6 mL of phosphorous oxychloride was heated on a steam bath for about 16 hours, then poured over ice. The mixture was neutralized with saturated sodium bicarbonate solution, then the solid was separated by filtration. The solid was dissolved in dilute hydrochloric acid, the mixture was filtered and the filtrate was neutralized with concentrated ammonium hydroxide to reprecipitate the product. Filtration and drying was followed by recrystallization from methanol to provide crystals of 4-chloro-1H-imidazo[4,5-c]-quinoline. Analysis: Calculated for C10 H6N3 : % C, 59.0; % H, 3.0; % N, 20.6; Found: % C, 59.5; % H, 3.0; % N, 20.2.

Workup

  1. temperaturewas heated on a steam bath for about 16 hours
  2. additionpoured over ice
  3. customthe solid was separated by filtration
  4. dissolutionThe solid was dissolved in dilute hydrochloric acid
  5. filtrationthe mixture was filtered
  6. filtrationFiltration
  7. customdrying
  8. customwas followed by recrystallization from methanol

Sources & evidence

ORD record
ord-ce975c41a88442ca86730bb9e13aaf5f
Source dataset
uspto-grants-1998_05
Patent number
US05756747

Reaction notes

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