Ethanol → HCID 178488018, compound

HRID 717352Notes

Reaction equation

HRID 717352 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=O)[C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=1)#[N:2].C([OH:26])C>OO.[OH-].[Na+]>[CH3:22][O:21][C:13]1[CH:12]=[C:11]([C:10]2[N:2]=[C:1]([OH:26])[C:3]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:9]=2)[CH:16]=[C:15]([O:17][CH3:18])[C:14]=1[O:19][CH3:20]

Participants

5

Reactant 2

HCID 702EthanolHCID 669673HCID 669673, compound

Product 1

HCID 178488018HCID 178488018, compound

Reagents, catalysts & solvents 2

HCID 784Hydrogen PeroxideSolventHCID 14798Sodium HydroxideSolvent

Procedure

Into a 1-L 3-necked round-bottom flask, was placed a solution of N-(2-cyanophenyl)-3,4,5-trimethoxybenzamide (22 g, 70.44 mmol, 1.00 equiv) in ethanol (200 mL), H2O2 (200 mL) and sodium hydroxide (200 mL, 20%). The resulting solution was stirred for 16 h at room temperature. The resulting mixture was concentrated under vacuum. The reaction was then quenched by the addition of 500 mL of water. The solids were collected by filtration. This resulted in 12 g (55%) of 2-(3,4,5-trimethoxyphenyl)quinazolin-4-ol as a white solid. MS (ESI) m/z 313 ([M+H]+).

Workup

  1. customInto a 1-L 3-necked round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customThe reaction was then quenched by the addition of 500 mL of water
  4. filtrationThe solids were collected by filtration
  5. customThis resulted in 12 g (55%) of 2-(3,4,5-trimethoxyphenyl)quinazolin-4-ol as a white solid

Sources & evidence

ORD record
ord-681eaed14a624454b069ec7753d9f9d9
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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