Sodium Hydroxide → 6-Fluoro-2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylic acid

HRID 717359Notes

Reaction equation

HRID 717359 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=1)[N:6]=[C:5]2[C:24]([O:26]C)=[O:25].[OH-].[Na+]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=1)[N:6]=[C:5]2[C:24]([OH:26])=[O:25]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 90411532Methyl 6-fluoro-2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylate

Product 1

HCID 904103076-Fluoro-2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 100-mL round-bottom flask, was placed methyl 6-fluoro-2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylate (1.0 g, 2.69 mmol, 1.00 equiv), tetrahydrofuran (10 mL) and sodium hydroxide (10 mL, 20%). The resulting solution was stirred for 0.5 h at room temperature. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with 100 mL of dichloromethane. The pH value of the solution was adjusted to 2 with hydrogen chloride (20%). The solids were collected by filtration. This resulted in 0.6 g (62%) of 6-fluoro-2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylic acid as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 3.75-3.80 (m, 3H), 3.91-3.96 (m, 6H), 7.89 (s, 2H), 8.02-8.07 (m, 1H), 8.22-8.27 (m, 2H); MS (ESI) m/z 359 ([M+H]+).

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. additionThe resulting solution was diluted with 100 mL of dichloromethane
  4. filtrationThe solids were collected by filtration
  5. customThis resulted in 0.6 g (62%) of 6-fluoro-2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylic acid as a yellow solid

Sources & evidence

ORD record
ord-948540397f5948f18e4bf5bc78b8d624
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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