4-Aminosalicylic Acid → Menthyl-para-aminosalicylate

HRID 259263Notes

Reaction equation

HRID 259263 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].[Na].NC1C=C(O)C(=CC=1)C([O-])=O.[K].NC1C=C(O)C(=CC=1)C([O-])=O.[Li].NC1C=C(O)C(=CC=1)C([O-])=O.CCl.[CH:50]1([CH3:60])[CH2:55][CH2:54][CH:53]([CH:56]([CH3:58])[CH3:57])[CH:52](Br)[CH2:51]1.C1(C)CCC(C(C)C)C(I)C1>[OH-].[Ag+]>[CH:50]1([CH3:60])[CH2:55][CH2:54][CH:53]([CH:56]([CH3:58])[CH3:57])[CH:52]([O:7][C:6](=[O:8])[C:5]2[C:4](=[CH:3][C:2]([NH2:1])=[CH:10][CH:9]=2)[OH:11])[CH2:51]1

Participants

9

Reactant 7

HCID 46494-Aminosalicylic AcidHCID 6327Methyl ChlorideHCID 557976Cyclohexane, 2-iodo-4-methyl-1-(1-methylethyl)-HCID 12847223MenthylbromideHCID 178507644HCID 178507644, compoundHCID 178507645HCID 178507645, compoundHCID 178507646HCID 178507646, compound

Product 1

HCID 54463918Menthyl-para-aminosalicylate

Reagents, catalysts & solvents 1

HCID 10129950Silver HydroxideCatalyst

Conditions

Temperature
50 °C

Procedure

One-tenth mol of an alkali metal salt of para-aminosalicylic acid as for example, sodium-p-aminosalicylate, potassium-p-aminosalicylate or lithium-p-aminosalicylate, is dissolved in 300 ml. of alcohol and to this is added exactly one-tenth mol of a menthyl halogen salt as for example, methyl chloride, menthyl bromide or menthyl iodide. The mixture is stirred and 0.5 gms. of freshly precipitated silver hydroxide is added as a catalyst. The mixture is warmed to 50° C. for a period of at least two hours, cooled to room temperature and filtered. The filtrate is set aside to crystallize in an ice-chest and menthyl-para-aminosalicylate is obtained as a white crystalline substance melting at 187° C. to 189° C. The compound is insoluble in water but soluble in alcohol, benzene and chloroform.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. customto crystallize in an ice-chest

Sources & evidence

ORD record
ord-1ad529b8589e40a5a693477d9e1b7ead
Source dataset
uspto-grants-1977_07
Patent number
US04036951

Reaction notes

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