Acetic Acid → 3-(2-Anilinopyrimidin-4-yl)benzoic acid

HRID 968684Notes

Reaction equation

HRID 968684 reaction equation
[C:1]1([NH:7][C:8]2[N:13]=[C:12]([C:14]3[CH:15]=C([CH:19]=[CH:20][CH:21]=3)C#N)[CH:11]=[CH:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[C:23]([OH:26])(=[O:25])[CH3:24]>>[C:1]1([NH:7][C:8]2[N:13]=[C:12]([C:14]3[CH:15]=[C:24]([CH:19]=[CH:20][CH:21]=3)[C:23]([OH:26])=[O:25])[CH:11]=[CH:10][N:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 671143483-(2-Phenylamino-pyrimidin-4-yl)benzonitrile

Product 1

HCID 694224873-(2-Anilinopyrimidin-4-yl)benzoic acidYield 84%

Conditions

Temperature
100 °C

Procedure

To a suspension of 3-(2-phenylamino-pyrimidin-4-yl)-benzonitrile (10 g, 36.7 mmol) in acetic acid (20 mL) was added concentrated hydrochloric acid (30 mL) and the suspension was heated at 100° C. overnight. The starting material completely dissolved and then a solid precipitated. The reaction mixture was filtered and precipitate was washed with ether and methanol to afford 9 g (84%) of the title compound.

Workup

  1. dissolutionThe starting material completely dissolved
  2. customa solid precipitated
  3. filtrationThe reaction mixture was filtered
  4. washprecipitate was washed with ether and methanol

Sources & evidence

ORD record
ord-fa98bb7481f744d3a9d46bed9915b813
Source dataset
uspto-grants-2007_12
Patent number
US07304071B2

Reaction notes

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