Oxalyl chloride → 4-Chloro-7-methoxy-6-(2-methoxyethoxy)-2-(3-nitrophenyl)quinazoline

HRID 1407015Notes

Reaction equation

HRID 1407015 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=O)[NH:8][C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=3)=[N:10]2)=[CH:5][C:4]=1[O:23][CH2:24][CH2:25][O:26][CH3:27].C(Cl)(=O)C([Cl:31])=O>C1COCC1.CN(C=O)C>[Cl:31][C:7]1[C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[C:4]([O:23][CH2:24][CH2:25][O:26][CH3:27])[CH:5]=2)[N:10]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[N:8]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 136203244HCID 136203244, compound

Product 1

HCID 593618974-Chloro-7-methoxy-6-(2-methoxyethoxy)-2-(3-nitrophenyl)quinazolineYield 68%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 7-methoxy-6-(2-methoxyethoxy)-2-(3-nitrophenyl)quinazolin-4(3H)-one (1.65 g, 4.46 mmol) in anhydrous THF (30 mL) was added oxalyl chloride (1.3 mL, 14.7 mmol) and 2 drops of DMF. The mixture was refluxed for 2 h, upon which the mixture was concentrated in vacuo, taken up in CHCl3 (100 mL) and washed with sat. NaHCO3 (3×50 mL), water (2×50 mL) and brine (1×50 mL). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo to give 4-chloro-7-methoxy-6-(2-methoxyethoxy)-2-(3-nitrophenyl)quinazoline (1.18 g, 3.03 mmol, 68%). HPLC retention time 9.55 mins.

Workup

  1. temperatureThe mixture was refluxed for 2 h, upon which the mixture
  2. concentrationwas concentrated in vacuo
  3. washwashed with sat. NaHCO3 (3×50 mL), water (2×50 mL) and brine (1×50 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1946ba8372534d2486351c0c9f9a47a8
Source dataset
uspto-grants-2014_12
Patent number
US08916576B2

Reaction notes

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