Hydrochloric Acid → (2-Chloromethyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine

HRID 2380994Notes

Reaction equation

HRID 2380994 reaction equation
[Cl:1][CH2:2][C:3]1[NH:12][C:11](=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.COC(=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH2:23].Cl[CH2:26]C#N.Cl.[O:30]1CCOC[CH2:31]1>>[Cl:1][CH2:2][C:3]1[N:12]=[C:11]([N:23]([C:18]2[CH:17]=[CH:22][C:21]([O:30][CH3:31])=[CH:20][CH:19]=2)[CH3:26])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 7856ChloroacetonitrileHCID 8635Methyl AnthranilateHCID 312751,4-DioxaneHCID 1354173742-(chloromethyl)quinazolin-4(3H)-one

Product 1

HCID 11358914(2-Chloromethyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amineYield 79.6%

Conditions

Temperature
80 °C

Procedure

2-Chloromethyl-quinazolin-4(3H)-one: To a solution of 2-amino-benzoic acid methyl ester (0.26 ml, 2 mmol) and chloro-acetonitrile (0.16 ml, 4.0 mmol) in dioxane (8 ml) at room temperature was added concentrated HCl (1.0 ml) dropwise. The mixture was heated at 80° C. for 24 h and then cooled to room temperature. The resulting solid was collected and dissolved in water (10 ml), and the solution was neutralized with 2 N NaOH aqueous to pH 7. The precipitation was collected by filtration, then washed with water and dried to give 309 mg (79.6%) of the title compound.

Workup

  1. temperaturecooled to room temperature
  2. customThe resulting solid was collected
  3. dissolutiondissolved in water (10 ml)
  4. customThe precipitation
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-08bc196edae1414e942d42f5e6509559
Source dataset
uspto-grants-2012_09
Patent number
US08258145B2

Reaction notes

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