Ammonia → Methyl 2-[2-(4-cyanophenyl)-ethyl]-quinazoline-7-carboxylate

HRID 50365Notes

Reaction equation

HRID 50365 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([NH:13][C:14]2[CH:15]=[C:16]([CH:22]=[CH:23][C:24]=2[CH:25]=O)[C:17]([O:19][CH2:20]C)=[O:18])=O)=[CH:5][CH:4]=1)#[N:2].[NH3:27]>>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:27]=[CH:25][C:24]3[C:14](=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:22][CH:23]=3)[N:13]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 18412494HCID 18412494, compound

Product 1

HCID 18412314Methyl 2-[2-(4-cyanophenyl)-ethyl]-quinazoline-7-carboxylate

Procedure

0.6 g (1.8 mmol) of ethyl 3-[3-(4-cyanophenyl)propionylamino]-4-formylbenzoate and 10 mL of methanolic ammonia solution were agitated in a pressure vessel for 36 hours. Then the solvent was distilled off, the residue was chromatographed on silica gel and eluted with methylene chloride containing 0 to 1% methanol. Yield: 0.35 g (62% of theory); Rf value: 0.38 (silica gel, ethyl acetate/cyclohexane=1:1).

Workup

  1. distillationThen the solvent was distilled off
  2. customthe residue was chromatographed on silica gel
  3. washeluted with methylene chloride containing 0 to 1% methanol

Sources & evidence

ORD record
ord-a23773213fd0416aa0ff633cbb18f28e
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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