Acetic Acid → 4-Hydroxybenzamide

HRID 1986605Notes

Reaction equation

HRID 1986605 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)C.C=O.C(O)(=O)C.[NH3:19]>CO>[OH:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]([NH2:19])=[O:3])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 712FormaldehydeHCID 8434Ethylparaben

Product 1

HCID 650524-Hydroxybenzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Parahydroxybenzoic acid ethyl ester is dissolved in methanol, added with formalin and acetic acid to react overnight, added to NH3(aq) to obtain para-hydroxy benzoic amide. This product was added with formalin, acetic acid and N7-bromoethyl 3-isobutyl-1-methylxanthine processed through a Mannich reaction to obtain compound 33. Through purification and then dissolution into methanol, add NaOH and ethyl bromide to gain compound 34. Various substitutions can be made to produce other desired compounds. For example, by replacing ethyl bromide with propyl bromide, compound 35 can be obtained. By replacing theophylline with IBMX, compounds 36, 37, and/or 38 can be obtained.

Workup

  1. customto react overnight

Sources & evidence

ORD record
ord-63322689126043b4856d1555c796c07b
Source dataset
uspto-grants-2009_06
Patent number
US07550468B2

Reaction notes

Loading…