Anthranilic Acid → HCID 21082444, compound

HRID 347286Notes

Reaction equation

HRID 347286 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH3:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH2:13].Cl.[OH-].[Na+]>O.[Cl-].[Zn+2].[Cl-]>[NH2:4][C:3]1[CH:5]=[CH:6][C:7]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([CH3:13])[CH3:11])=[CH:8][C:2]=1[C:1]([OH:10])=[O:9]

Participants

7

Reactant 4

HCID 227Anthranilic AcidHCID 313Hydrochloric AcidHCID 7407Alpha-MethylstyreneHCID 14798Sodium Hydroxide

Product 1

HCID 21082444HCID 21082444, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of anthranilic acid (82 g, 0.6 mol), α-methylstyrene (168 mL, 1,28 mol), zinc chloride (82 g, 0.6 mol) and concentrated hydrochloric acid (100 mL) is heated to 120° C. for four hours. The mixture is cooled and diluted with water (100 mL). The pH is adjusted to approximately 4 using 50% sodium hydroxide. The resulting solids are collected, washed with water and then partitioned between methylene chloride and water. The pH is adjusted to 5–6 with dilute hydrochloric acid giving two clear phases. The organic phase is separated and then dried over anhydrous sodium sulfate. The methylene chloride is removed and the solid residue obtained is recrystallized from heptane/toluene giving the title intermediate compound as a white solid melting at 142–144° C.

Workup

  1. temperatureThe mixture is cooled
  2. customThe resulting solids are collected
  3. washwashed with water
  4. custompartitioned between methylene chloride and water
  5. customThe organic phase is separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe methylene chloride is removed
  8. customthe solid residue obtained
  9. customis recrystallized from heptane/toluene giving the title intermediate compound as a white solid melting at 142–144° C.

Sources & evidence

ORD record
ord-0be1f3fde4584950bf0a82ee7ede7026
Source dataset
uspto-grants-2007_02
Patent number
US07173128B2

Reaction notes

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