Hydrochloric Acid → HCID 86675665, compound

HRID 2283134Notes

Reaction equation

HRID 2283134 reaction equation
C([NH:4][C:5]1[C:6](=[C:10]([I:14])[CH:11]=[CH:12][CH:13]=1)[C:7]([OH:9])=[O:8])(=O)C.[ClH:15]>>[ClH:15].[I:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:5]([NH2:4])[C:6]=1[C:7]([OH:9])=[O:8]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 71208719HCID 71208719, compound

Product 1

HCID 86675665HCID 86675665, compound

Procedure

Charge a 12 L, 3-neck flask, equipped with a stirrer, condenser, heating mantle and thermometer with N-Acetyl-6-Iodo-Anthranilic acid (400 grams) and 2.5 L concentrated HCl. Adjust the temperature to 50-55° C. and maintain for 24 hours. Higher temperatures may decompose the product. Chill the reaction to less than 5° C. in an ice bath, filter the product, wash the filter “cake” with acetone, then diethylether. Air dry the product. Yield was 340 grams. (Theoretical yield=374.4 grams). Melting point (m.p.) at 176-180° C.

Workup

  1. additionCharge a 12 L, 3-neck flask
  2. customequipped with a stirrer, condenser
  3. customto 50-55° C.
  4. temperaturemaintain for 24 hours
  5. temperatureChill
  6. customthe reaction to less than 5° C. in an ice bath
  7. filtrationfilter the product
  8. washwash the
  9. filtrationfilter “cake” with acetone
  10. customAir dry the product
  11. customat 176-180° C.

Sources & evidence

ORD record
ord-e1b2070f8933452b8157f7206bab5ae3
Source dataset
uspto-grants-2015_09
Patent number
US09144613B2

Reaction notes

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