Salicylic Acid → HCID 13066649, compound

HRID 1606642Notes

Reaction equation

HRID 1606642 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([NH2:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].P(Cl)(Cl)Cl.[C:17]([OH:26])(=O)[C:18]1[C:19](=[CH:21][CH:22]=[CH:23][CH:24]=1)[OH:20]>N1C=CC=CC=1>[C:17]([NH:1][C:2]1[CH:11]=[C:10]([NH:12][C:17](=[O:26])[C:18]2[C:19](=[CH:21][CH:22]=[CH:23][CH:24]=2)[OH:20])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])(=[O:26])[C:18]1[C:19](=[CH:21][CH:22]=[CH:23][CH:24]=1)[OH:20]

Participants

5

Reactant 3

HCID 338Salicylic AcidHCID 24387Phosphorus trichlorideHCID 12399493Methyl 2,4-diaminobenzoate

Product 1

HCID 13066649HCID 13066649, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
90 °C

Procedure

In 200 ml of pyridine was dissolved 8.3 g of methyl 2,4-diaminobenzoate, and to the solution was added a solution of 4.4 ml of phosphorus trichloride in 30 ml of pyridine under cooling with ice, followed by stirring at 50° to 70°C for one hour. To the mixture was added 21 g of salicylic acid was added, followed by heating at 90°C for three hours. After the cooling of the mixture by allowing it to stand, undissolved substances were filtered off and the filtrate was subjected to concentrate under reduced pressure. The concentrate was added to cold diluted hydrochloric acid to precipitate crystals. The crystals were recovered by filtration, washed with water and recrystallized from an acetone-dioxane-water mixture to obtain 11.1 g of methyl 2,4-bis(salicylamido)-benzoate having a melting point between 259° - 260°C. It was confirmed that the product was identical to that obtained in Example 7.

Workup

  1. temperatureunder cooling with ice
  2. additionwas added
  3. temperatureAfter the cooling of the mixture
  4. filtrationundissolved substances were filtered off
  5. concentrationto concentrate under reduced pressure
  6. additionThe concentrate was added to cold diluted hydrochloric acid
  7. customto precipitate crystals
  8. filtrationThe crystals were recovered by filtration
  9. washwashed with water
  10. customrecrystallized from an acetone-dioxane-water mixture

Sources & evidence

ORD record
ord-029b099ba04346f9bf1b4dd807bcd6fb
Source dataset
uspto-grants-1976_04
Patent number
US03953496

Reaction notes

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