Hydrochloric Acid → HCID 13912874, compound

HRID 1789075Notes

Reaction equation

HRID 1789075 reaction equation
[NH2:1][C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[K+].Cl>O1CCOCC1.O>[NH2:1][C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 1288398779893-21-3

Product 1

HCID 13912874HCID 13912874, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 13.57 g of methyl 5-amino-2-methoxy-4-nitrobenzoate in 250 ml of dioxane was added a solution of 4.36 g of potassium hydroxide in 25 ml of water, and the mixture was refluxed for 4 hours. To the reaction solution was added 7 ml of concentrated hydrochloric acid. The solvent was evaporated under reduced pressure, and the residue, after addition of dioxane, was refluxed for an hour. The insoluble was removed by filtration, and the filtrate was allowed to stand to give the title compound, m.p. 252°-255° C., yield of 10.99 g.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customThe solvent was evaporated under reduced pressure
  3. additionthe residue, after addition of dioxane
  4. temperaturewas refluxed for an hour
  5. customThe insoluble was removed by filtration

Sources & evidence

ORD record
ord-a170a4be891f44c2bc90932bb1a45f78
Source dataset
uspto-grants-1987_08
Patent number
US04686292

Reaction notes

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