Hydrochloric Acid → 3,4-Dimethoxycinnamohydroxamic acid

HRID 620406

Reaction equation

HRID 620406 reaction equation
Cl.[NH2:2][OH:3].[OH-].[K+].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH:11]=[CH:12][C:13](OC)=[O:14].Cl>CO>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH:11]=[CH:12][C:13]([NH:2][OH:3])=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 94307Methyl 3,4-dimethoxycinnamateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 329133,4-Dimethoxycinnamohydroxamic acidYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of hydroxylamine hydrochloride (5.09 g, 72 mmol) in methanol (26 ml) was added to a solution of 88% potassium hydroxide (6.99 g, 109 mmol) in methanol (15.3 ml), keeping the temperature below 40° C. The mixture was cooled to 0° C., filtered, and methyl 3,4-dimethoxycinnamate (8.0 g, 36 mmol) was added to the filtrate. After two hours, concentrated HCl (5 ml) was added to the cold solution. The resulting precipitate was filtered, washed with water and ether, and dried in vacuo, to give 6.74 g (84% yield) of the named compound, mp 183°-185° C.

Workup

  1. customthe temperature below 40° C
  2. filtrationfiltered
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water and ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-0ccc845c683e4ffc8d6174324d73e56a
Source dataset
uspto-grants-1989_04
Patent number
US04820828

Linked notes

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