Water → 2-Chloro-N-(4-methylphenyl)quinazolin-4-amine

HRID 408885Notes

Reaction equation

HRID 408885 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:13]([O-])(=O)[CH3:14].[K+].O>C1COCC1.O>[Cl:1][C:2]1[N:11]=[C:10]([NH:3][C:4]2[CH:9]=[CH:8][C:13]([CH3:14])=[CH:6][CH:5]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2528862,4-DichloroquinazolineHCID 517044Potassium Acetate

Product 1

HCID 226926752-Chloro-N-(4-methylphenyl)quinazolin-4-amineYield 144.8%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of 2,4-dichloroquinazoline (5.8 g, 0.029 mol), p-tolyamine (3.5 g, 0.032 mol), and potassium acetate (3.72 g, 0.038 mol) in THF/water (66 ml/30 ml) was stirred at room temperature for 16 h. Water (66 ml) was added to the mixture, and a precipitate was formed. The precipitate was washed with water, filtered, and dried under high vacuum to afford (2-chloro-quinazolin-4-yl)-p-tolyl-amine (5.65 g, 0.021 mol, 70%). m.p.: 198-199° C.; 1H NMR (300 MHz, DMSO-d6) δ 2.27 (s, 3H), 7.21 (d, J=7.8 Hz, 2H), 7.50 (d, J=7.2 Hz, 3H), 7.83 (t, J=8.5 Hz, 2H), 8.50 (t, J=8.0 Hz, 1H).

Workup

  1. customa precipitate was formed
  2. washThe precipitate was washed with water
  3. filtrationfiltered
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-d59aed6da692463d826919848a90a849
Source dataset
uspto-grants-2014_06
Patent number
US08759363B2

Reaction notes

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