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

HRID 1436267
Notes
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Reaction equation

HRID 1436267 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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-b5221fa41b004094aa665a783165350c
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07618975B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes