Hydrochloric Acid → HCID 2975401, compound

HRID 1662933Notes

Reaction equation

HRID 1662933 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:11]([OH:13])=O)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.Cl>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:8][C:9]3[C:10](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:11](=[O:13])[C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 120159Anthranilic acid, N-(p-fluorophenyl)-

Product 1

HCID 2975401HCID 2975401, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
115 °C

Procedure

N-(4-Fluorophenyl)anthranilic acid (0.70 gm; 3 mmol) and phosphorous oxychloride (3 ml) were stirred together and heated to 115° C. for 3.5 hours, then allowed to cool. The reaction mixture was placed on ice and small pieces of ice added, a vigorous reaction occurred with the evolution of hydrogen chloride. When the reaction had subsided, water (15 ml) was added and the mixture was boiled for 2 hours. On cooling, a solid precipitated out. This was filtered off and washed with water until the filtrate was colourless. The precipitate was further washed with cold methanol then diethyl ether and dried under vacuum to give 383 mg (59%) of 2-fluoroacridone.

Workup

  1. temperatureto cool
  2. additionadded
  3. customa vigorous reaction
  4. temperatureOn cooling
  5. customa solid precipitated out
  6. filtrationThis was filtered off
  7. washwashed with water until the filtrate
  8. washThe precipitate was further washed with cold methanol
  9. dry with materialdiethyl ether and dried under vacuum

Sources & evidence

ORD record
ord-179491eb24b5448d80015da91d822e3f
Source dataset
uspto-grants-2011_10
Patent number
US08034558B2

Reaction notes

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