Tetrahydrofuran → 2-(4-Fluorophenyl)quinazoline-4-carboxylic acid

HRID 717326Notes

Reaction equation

HRID 717326 reaction equation
[F: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.O1CCCC1>O>[F: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 8028TetrahydrofuranHCID 90410278Ethyl 2-(4-fluorophenyl)quinazoline-4-carboxylate

Product 1

HCID 904114972-(4-Fluorophenyl)quinazoline-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
26 °C

Procedure

Into a 500-mL 3-necked round-bottom flask, was placed ethyl 2-(4-fluorophenyl)quinazoline-4-carboxylate (15 g, 50.63 mmol, 1.00 equiv), oxolane (150 mL), lithiumol (2.4 g, 100.22 mmol, 2.00 equiv) and water (50 mL). The resulting solution was stirred overnight at 26° C. The resulting mixture was concentrated under vacuum. The pH value of the solution was adjusted to 5 with hydrogen chloride (2 mol/L). The solids were collected by filtration and washed with water. This resulted in 10 g (74%) of 2-(4-fluorophenyl)quinazoline-4-carboxylic acid as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 7.37-7.41 (m, 2H), 7.65-7.69 (m, 1H), 7.96-8.03 (m, 2H), 8.20-8.22 (m, 1H), 8.56-8.61 (m, 2H); MS (ESI) m/z 269 ([M+H]+).

Workup

  1. customInto a 500-mL 3-necked round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. filtrationThe solids were collected by filtration
  4. washwashed with water
  5. customThis resulted in 10 g (74%) of 2-(4-fluorophenyl)quinazoline-4-carboxylic acid as a yellow solid

Sources & evidence

ORD record
ord-c3018e18b680420a9851ed585209e1d4
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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