Sodium Methoxide → N-(3-Ethynylphenyl)-7-methoxy-6-nitroquinazolin-4-amine

HRID 1288896Notes

Reaction equation

HRID 1288896 reaction equation
Cl.Cl[C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]#[CH:21])[CH:15]=3)=[N:8][CH:9]=[N:10]2)=[CH:5][C:4]=1[N+:22]([O-:24])=[O:23].[CH3:25][O-:26].[Na+]>O>[C:20]([C:16]1[CH:15]=[C:14]([NH:13][C:7]2[C:6]3[C:11](=[CH:12][C:3]([O:26][CH3:25])=[C:4]([N+:22]([O-:24])=[O:23])[CH:5]=3)[N:10]=[CH:9][N:8]=2)[CH:19]=[CH:18][CH:17]=1)#[CH:21]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18925030HCID 18925030, compound

Product 1

HCID 18925009N-(3-Ethynylphenyl)-7-methoxy-6-nitroquinazolin-4-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

(7-Chloro-6-nitroquinazolin-4-yl)-(3-ethynyl-phenyl)-amine hydrochloride (100 mg, 0.306 mmol and dry sodium methoxide (120 mg, 2.22 mmol) were stirred in 2 mL of dry 2-methylpyrrolidin-1-one for 8 hours at 30° C. To the cooled reaction mixture 0.93 mL of 3N and 1 mL of water were added. The mixture was diluted with 60 mL of water and extracted with two time 60 mL of ethyl acetate. The pooled organic layers were washed with three times 50 mL of water and 50 mL of brine, dried with magnesium sulfate, filtered and vacuum evaporated to afford the title product as a solid; 80 mg (82%); mp 213°-218° C. dec.

Workup

  1. additionwere added
  2. extractionextracted with two time 60 mL of ethyl acetate
  3. washThe pooled organic layers were washed with three times 50 mL of water and 50 mL of brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. customvacuum evaporated

Sources & evidence

ORD record
ord-7741e995d72d4983a2116b7e3fef8344
Source dataset
uspto-grants-1998_05
Patent number
US05747498

Reaction notes

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