Ammonia → HCID 13255229, compound

HRID 462667Notes

Reaction equation

HRID 462667 reaction equation
[CH:1]([C:3]1[CH:13]=[C:12]([CH3:14])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:5]([CH3:15])[C:4]=1[NH:16][C:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:24])=O.[NH3:26]>C(O)C>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:17]1[N:26]=[CH:1][C:3]2[C:4](=[C:5]([CH3:15])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:12]([CH3:14])[CH:13]=2)[N:16]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 13255228HCID 13255228, compound

Product 1

HCID 13255229HCID 13255229, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

504 mg of ethyl 4-formyl-2,6-dimethyl-3-(o-chlorobenzoylamino)benzoate was dissolved in 50 ml of ethanol saturated with ammonia and the solution was left to stand overnight at room temperature. The solvent was evaporated, and the residue was separated and purified by silica gel column chromatography. Fractions eluted with diethyl ether/n-hexane (volume ratio 2:8) were collected and the solvent was evaporated. The residue was recrystallized from methanol/n-hexane to give 150 mg (yield 30%) of 2-(o-chlorophenyl)-7-ethoxycarbonyl-6,8-dimethylquinazoline having a melting point of 69.5° to 70.5° C.

Workup

  1. waitthe solution was left
  2. customThe solvent was evaporated
  3. customthe residue was separated
  4. custompurified by silica gel column chromatography
  5. washFractions eluted with diethyl ether/n-hexane (volume ratio 2:8)
  6. customwere collected
  7. customthe solvent was evaporated
  8. customThe residue was recrystallized from methanol/n-hexane

Sources & evidence

ORD record
ord-d360c36b36cf4c519f2993988db124bd
Source dataset
uspto-grants-1985_05
Patent number
US04517189

Reaction notes

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