Ammonia → 2-Hydroxy-4-methylbenzamide

HRID 1460980Notes

Reaction equation

HRID 1460980 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([O:11]CCC)[CH:3]=1.CC1C=C(O)C(=CC=1)C(OC)=O.N>>[CH3:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([NH2:8])=[O:7]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 78400Benzoic acid, 2-hydroxy-4-methyl-, methyl esterHCID 212507564-Methyl-2-propoxybenzamide

Product 1

HCID 105348392-Hydroxy-4-methylbenzamide

Procedure

The starting-material, 4-methyl-2-propoxybenzamide, was prepared by reacting methyl 4-methylsalicylate (25.75 g) with ethanolic ammonia to yield 4-methylsalicylamide (12.54 g) which was then reacted with bromopropane, potassium iodide and potassium carbonate in acetone.

Sources & evidence

ORD record
ord-c1790cb5b8c24807ad86386895fad726
Source dataset
uspto-grants-1991_12
Patent number
US05073559

Reaction notes

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