Hydrochloric Acid → HCID 12215093, compound

HRID 484085Notes

Reaction equation

HRID 484085 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1.Cl>C(OCCO)C.O.[Cu]>[C:23]1([CH3:26])[CH:24]=[CH:25][C:20]([NH:19][C:2]2[C:3](=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=2)[C:4]([OH:6])=[O:5])=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7813p-ToluidineHCID 11430Potassium CarbonateHCID 2215032-Chloro-5-methoxybenzoic acid

Product 1

HCID 12215093HCID 12215093, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolventHCID 8076Glycol monoethyl etherSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-chloro-5-methoxybenzoic acid (14.0 g, 80.0 mmol), potassium carbonate (13.8 g, mol), powdered copper (1.5 g), cuprous oxide (1.5 g), and p-toluidine (9.4 g, 88.0 mmol) in 2-ethoxyethanol (120 ml) is heated at 140° C. for 3 hours. After cooling, the dark mixture is acidified to about pH 2 with 1N hydrochloric acid, and then diluted with water (600 ml). The solid precipitates are collected by filtration, dissolved in hot 10% sodium carbonate solution, charcoaled, and filtered through a Celite bed. The filtrate is acidified with concentrated hydrochloric acid to about pH 2, and the mixture is extracted with ethyl ether (5×100 ml). The combined extracts are washed with 1N hydrochloric acid (200 ml) and water (2×200 ml), dried over sodium sulfate, concentrated in vacuo, and the solid residue is recrystallized from ethanol-water to give N-(p-tolyl)-5-methoxyanthranilic acid (13.9 g, 68% yield), mp 160° -161° C.

Workup

  1. temperatureAfter cooling
  2. customThe solid precipitates
  3. filtrationare collected by filtration
  4. dissolutiondissolved in hot 10% sodium carbonate solution
  5. filtrationfiltered through a Celite bed
  6. extractionthe mixture is extracted with ethyl ether (5×100 ml)
  7. washThe combined extracts are washed with 1N hydrochloric acid (200 ml) and water (2×200 ml)
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customthe solid residue is recrystallized from ethanol-water

Sources & evidence

ORD record
ord-8e5c86c7f0f142e38f58c08178a38ae6
Source dataset
uspto-grants-1993_07
Patent number
US05229395

Reaction notes

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