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

HRID 330796Notes

Reaction equation

HRID 330796 reaction equation
S(=O)(=O)(O)[OH:2].CN(C=N[C:11]1[CH:12]=[N:13][C:14]([C:17]2[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=2)[C:20]([O:22]C)=[O:21])=[N:15][CH:16]=1)C>O>[OH:2][C:11]1[CH:12]=[N:13][C:14]([C:17]2[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=2)[C:20]([OH:22])=[O:21])=[N:15][CH:16]=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 962WaterSolvent2×

Procedure

160 ml (2.88 mol) of concentrated sulfuric acid are added to a suspension of 103.5 g (364 mmol) of methyl 3-[5-(dimethylaminomethyleneamino)pyrimidin-2-yl]benzoate in 1.3 l of water, and the mixture is heated at the boil for 4 hours. The reaction mixture is cooled to room temperature, diluted with water and filtered off with suction. The residue is washed with water and dried in vacuo: 3-(5-hydroxypyrimidin-2-yl)benzoic acid as brownish crystals; m.p. 293-295°; ESI 217 (M+H); HPLC: Rt.=2.19 min (method A).

Workup

  1. temperaturethe mixture is heated at the boil for 4 hours
  2. filtrationfiltered off with suction
  3. washThe residue is washed with water
  4. customdried in vacuo
  5. custom=2.19 min (method A)

Sources & evidence

ORD record
ord-61a0a40cb8dc40a0a3e9bca79d2008e7
Source dataset
uspto-grants-2014_11
Patent number
US08877751B2

Reaction notes

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