Ammonium Chloride → HCID 58075442, compound

HRID 2370212Notes

Reaction equation

HRID 2370212 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[CH2:8][CH2:7][CH2:6][CH:5]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C:4]=2[N:3]=1.[Cl-].[NH4+]>CC(C)=O.O.[Zn]>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH:5]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C:4]=2[N:3]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 58075728HCID 58075728, compound

Product 1

HCID 58075442HCID 58075442, compoundYield 19.67%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2,4-dichloro-8-(4-fluorophenyl)-5,6,7,8-tetrahydroquinazoline (115 mg, 0.387 mmol), Ammonium chloride (26.9 mg, 0.503 mmol) and zinc (266 mg, 4.06 mmol) in acetone (1 mL) and water (1.000 mL) was heated at 90° C. with stirring for 2 h. The reaction mixture was filtered through a short plug of celite. The solvent was removed in vacuum, and the residue was partitioned between dichloromethane and water. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic extracts were dried over anhydrous magnesium sulfate and filtered. The solvent was removed in vacuum and the residue was purified by column chromatography on silica gel to give 2-chloro-8-(4-fluorophenyl)-5,6,7,8-tetrahydroquinazoline (20 mg, 0.076 mmol, 19.67% yield) as a white solid. LC-MS (M+H)+=263.2.

Workup

  1. filtrationThe reaction mixture was filtered through a short plug of celite
  2. customThe solvent was removed in vacuum
  3. customthe residue was partitioned between dichloromethane and water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with dichloromethane
  6. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed in vacuum
  9. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-fea07b900f0547209097c19ee7a880ff
Source dataset
uspto-grants-2014_04
Patent number
US08710061B2

Reaction notes

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