Hydrochloric Acid → 3-Chloro-4-hydroxybenzamide

HRID 70288Notes

Reaction equation

HRID 70288 reaction equation
C(=O)(OC(C)(C)C)[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH2:11])=[O:10])=[CH:5][C:4]=1[Cl:12].Cl>O1CCOCC1>[Cl:12][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:3]=1[OH:2])[C:9]([NH2:11])=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67159970HCID 67159970, compound

Product 1

HCID 229323473-Chloro-4-hydroxybenzamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of 4-(aminocarbonyl)-2-chlorophenyl 1,1-dimethylethyl carbonate (6.86 g, 0.025 mol) and 4N HCl in dioxane (50 mL) in dioxane (30 mL) was heated at reflux for 4 hr. The reaction mixture was cooled, and precipitated solid was collected by filtration affording 3-chloro-4-hydroxybenzamide as a white solid, used without further purification. LC/MS (method E) tR 0.88 min; m/z 172 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hr
  3. temperatureThe reaction mixture was cooled
  4. customprecipitated solid
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-c74f1cf6b8434063a54c1d8113030b1e
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Reaction notes

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