Sodium Hydroxide → Quinazolin-8-amine

HRID 513745Notes

Reaction equation

HRID 513745 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][N:10]=[C:9]2NNS(C1C=CC(C)=CC=1)(=O)=O>CCO>[N:12]1[C:13]2[C:8](=[CH:7][CH:6]=[CH:5][C:4]=2[NH2:3])[CH:9]=[N:10][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68183283N'-(8-aminoquinazolin-4-yl)-4-methylbenzene-1-sulfonohydrazide

Product 1

HCID 11344089Quinazolin-8-amineYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1N NaOH (9 ml) was added to a solution of N′-(8-aminoquinazolin-4-yl)-4-methylbenzene-1-sulfonohydrazide 479 (300 mg, 9.1 mmol) in EtOH (20 ml) and the mixture was heated under reflux for 3 h. After cooling, the mixture was concentrated in vacuo. The residue was diluted with water (10 ml) and the aqueous phase was extracted with EtOAc. The organic phase was washed with brine, dried (Na2SO4), and concentrated in vacuo to give title compound (140 mg, 76%) which was used in the next step without further purification. The structure was confirmed by 1H NMR.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 h
  3. temperatureAfter cooling
  4. concentrationthe mixture was concentrated in vacuo
  5. additionThe residue was diluted with water (10 ml)
  6. extractionthe aqueous phase was extracted with EtOAc
  7. washThe organic phase was washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3b3a9f7fdee54405a7dea6e15cbee1f6
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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