Anthranilic Acid → HCID 385601, compound

HRID 427599Notes

Reaction equation

HRID 427599 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[C:11]([C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=O)=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].Cl>N1C=CC=CC=1>[C:11]([C:15]1[CH:16]=[CH:17][C:18]([C:19]2[O:9][C:1](=[O:10])[C:2]3[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=3[N:4]=2)=[CH:22][CH:23]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 227Anthranilic AcidHCID 313Hydrochloric AcidHCID 743724-tert-Butylbenzoyl chloride

Product 1

HCID 385601HCID 385601, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of anthranilic acid (34.3 g, 250 mmol) in pyridine (400 mL) was added 4-tert-butylbenzoyl chloride (94 mL, 500 mL) dropwise via an addition funnel. After stirring for 12 h, the solution was poured onto a slurry of ice and 2 N aqueous hydrochloric acid (100 mL). The mixture was extracted with dichloromethane and the organic extract was concentrated in vacuo. The residue was dissolved in fresh dichloromethane, washed once with 2 N aqueous hydrochloric acid, once with saturated aqueous sodium chloride solution, twice with saturated aqueous sodium bicarbonate solution, three times with water, dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was crystallized from ether/hexanes to give an initial crop of 15.2 g (22%) of the title compound as an off-white solid, followed by additional crops totalling 16.9 g (24%).

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. extractionthe organic extract
  3. concentrationwas concentrated in vacuo
  4. dissolutionThe residue was dissolved in fresh dichloromethane
  5. washwashed once with 2 N aqueous hydrochloric acid, once with saturated aqueous sodium chloride solution, twice with saturated aqueous sodium bicarbonate solution, three times with water
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was crystallized from ether/hexanes

Sources & evidence

ORD record
ord-6491876dd8614dc19005c4d4ffde2617
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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