Hydrochloric Acid → HCID 67786350, compound

HRID 1763058Notes

Reaction equation

HRID 1763058 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-])=O.[ClH:14].[H][H]>[Pd].O>[OH2:1].[ClH:14].[NH2:11][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[OH:1])[C:6]([OH:8])=[O:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 120334-Hydroxy-3-nitrobenzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 67786350HCID 67786350, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

To a 5-liter, 3-necked, round-bottom flask is added 160 g of 4-hydroxy-3-nitrobenzoic acid, 150 cc concentrated hydrochloric acid, 3 liters of distilled water and 25 g of 5 percent palladium on carbon. The reaction mixture is heated to 95° C. with vigorous stirring and hydrogen gas is passed into the reaction mixture. Upon completion, the reaction is cooled to room temperature under nitrogen gas and the catalyst is recovered by filtration. The resulting solution is poured into two 4-liter beakers and acidified with concentrated hydrochloric acid to a normality of 4 and allowed to cool to 0° C. The resulting solid is isolated by filtration and dried under vacuum to afford 176 g of crude 3-amino-4-hydroxybenzoic acid hydrochloride monohydrate with a melting point of 300° C. decomposition.

Workup

  1. temperatureUpon completion, the reaction is cooled to room temperature under nitrogen gas
  2. filtrationthe catalyst is recovered by filtration
  3. additionThe resulting solution is poured into two 4-liter beakers
  4. temperatureto cool to 0° C
  5. customThe resulting solid is isolated by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-58998b2613da4498853b666a7f9ccfc6
Source dataset
uspto-grants-1989_05
Patent number
US04835306

Reaction notes

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