Sulfuric Acid → 3-(5-Hydroxypyrimidin-2-yl)benzoic acid

HRID 1509844Notes

Reaction equation

HRID 1509844 reaction equation
CN(C=N[C:6]1[CH:7]=[N:8][C:9]([C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=2)[C:15]([O:17]C)=[O:16])=[N:10][CH:11]=1)C.S(=O)(=O)(O)[OH:23]>O>[OH:23][C:6]1[CH:7]=[N:8][C:9]([C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=2)[C:15]([OH:17])=[O:16])=[N:10][CH:11]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 594848583-[5-(((Dimethylamino)methylene)amino)pyrimidin-2-yl]benzoic acid methyl ester

Product 1

HCID 594849363-(5-Hydroxypyrimidin-2-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

103.5 g of methyl 3-[5-(dimethylaminomethylenamino)pyrimidin-2-yl]benzoate (364.04 mmol) are suspended in 1300 ml of water in a 2 l single-necked flask, and 160 ml of conc. sulfuric acid (95-97%) (2.88 mol) are subsequently added, and the reaction batch is warmed at 130° C. (oil-bath temperature) for 4 h. For work-up, the reaction batch is cooled, and the precipitate formed is filtered off, washed with water and dried at 50° C. in a vacuum drying cabinet.

Workup

  1. temperatureFor work-up, the reaction batch is cooled
  2. customthe precipitate formed
  3. filtrationis filtered off
  4. washwashed with water
  5. customdried at 50° C. in a vacuum
  6. customdrying cabinet

Sources & evidence

ORD record
ord-93f89fb81e304d95a9938164b421c2f5
Source dataset
uspto-grants-2012_07
Patent number
US08211886B2

Reaction notes

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