Sodium Hydroxide → 2-(4-Methylphenyl)quinazoline-4-carboxylic acid

HRID 717329Notes

Reaction equation

HRID 717329 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]=[C:16]([C:18]([O:20]CC)=[O:19])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]=[C:16]([C:18]([OH:20])=[O:19])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 90410917Ethyl 2-(p-tolyl)quinazoline-4-carboxylate

Product 1

HCID 904111782-(4-Methylphenyl)quinazoline-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 150-mL 3-necked round-bottom flask, was placed a solution of ethyl 2-(4-methylphenyl)quinazoline-4-carboxylate (2.64 g, 9.03 mmol, 1.00 equiv) in ethanol (50 mL). This was followed by the addition of sodium hydroxide (1.8 g, 45.00 mmol, 5.00 equiv, 20%) dropwise with stirring at room temperature. The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum. The residue was diluted with 50 mL of water. Hydrogen chloride (5%) was employed to adjust the pH to 3-4. The solids were collected by filtration. This resulted in 2.30 g (96%) of 2-(4-methylphenyl)quinazoline-4-carboxylic acid as a light green solid. MS (ESI) m/z 265 ([M+H]+).

Workup

  1. customInto a 150-mL 3-necked round-bottom flask, was placed
  2. stirringThe resulting solution was stirred overnight at room temperature
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. additionThe residue was diluted with 50 mL of water
  5. filtrationThe solids were collected by filtration
  6. customThis resulted in 2.30 g (96%) of 2-(4-methylphenyl)quinazoline-4-carboxylic acid as a light green solid

Sources & evidence

ORD record
ord-cfeb4cbfb20e471ea753ac3b4e4a2ebc
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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