Hydrochloric Acid → HCID 178487747, compound

HRID 241034Notes

Reaction equation

HRID 241034 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.[Cl:14][CH2:15][C:16]#[N:17].Cl>C(OCC)C>[ClH:14].[Cl:14][CH2:15][C:16]1[N:17]=[C:4]([OH:6])[C:3]2[C:2](=[CH:11][C:10]([O:12][CH3:13])=[CH:9][CH:8]=2)[N:1]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7856ChloroacetonitrileHCID 12919999Methyl 2-amino-4-methoxybenzoate

Product 1

HCID 178487747HCID 178487747, compoundYield 127.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of methyl 2-amino-4-methoxybenzoate (5.4 g, 30.0 mmol) and chloroacetonitrile (2.8 mL, 45.0 mmol) was added anhydrous hydrogen chloride (4M solution in 1,4-dioxane, 20.0 mL, 80 mmol) and the reaction mixture was stirred at 50° C. for 30 minutes. After cooling it to room temperature the resulting slurry was diluted with diethyl ether (100 mL) and the stirring was continued for an additional 30 minutes. The off-white precipitate was collected by filtration, washed with diethyl ether and dried in vacuo to provide 2-(chloromethyl)-7-(methyloxy)quinazolin-4-ol hydrochloride (7.5 g, 96%). MS (EI) for C10H9ClN2O2: 225 (MH+).

Workup

  1. temperatureAfter cooling it to room temperature the resulting slurry
  2. waitthe stirring was continued for an additional 30 minutes
  3. filtrationThe off-white precipitate was collected by filtration
  4. washwashed with diethyl ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-81fd18f498894eb1b41a5736ea664efb
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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