Sodium Hydroxide → HCID 178487952, compound

HRID 1520317Notes

Reaction equation

HRID 1520317 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.[OH-:15].[Na+]>C1COCC1>[Cl:1][C:2]1[N:11]=[C:10]([OH:15])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 99913972,4-Dichloro-6-methoxyquinazoline

Product 1

HCID 178487952HCID 178487952, compoundYield 102.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2,4-dichloro-6-methoxyquinazoline (4.20 g, 18.5 mmol, 1.0 eq.) in THF (60 mL) and 1120 (60 mL) was treated with NaOH (4.00 g, 100 mmol, 5.4 eq.). The resulting mixture was stirred at 40° C. for 2 h. The reaction color turned to dark green and then a precipitate formed. After the reaction was completed, the mixture was cooled to room temperature. The precipitate was filtered off and the filtrate was concentrated down to 60 mL. The pH was then adjusted to 6 by adding 2N HCl in water. The precipitate which formed was collected and dried in vacuo to give 4.00 g of 2-chloro-6-methoxyquinazolin-4-ol as a grey solid (98%). LCMS m/z=211.1, 213.0 (M+1) (Method B) (retention time=1.11 min).

Workup

  1. customformed
  2. temperaturethe mixture was cooled to room temperature
  3. filtrationThe precipitate was filtered off
  4. concentrationthe filtrate was concentrated down to 60 mL
  5. additionby adding 2N HCl in water
  6. customThe precipitate which formed
  7. customwas collected
  8. customdried in vacuo

Sources & evidence

ORD record
ord-0327c0a10f8b43828d8839ba2006e7e4
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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