Benzenamine, 3-ethynyl- → N-(3-Ethynylphenyl)-2H-[1,3]dioxolo[4,5-g]quinazolin-8-amine

HRID 1249745Notes

Reaction equation

HRID 1249745 reaction equation
Cl[C:2]1[C:11]2[CH:10]=[C:9]3[O:12][CH2:13][O:14][C:8]3=[CH:7][C:6]=2[N:5]=[CH:4][N:3]=1.[C:15]([C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20])#[CH:16]>C(O)(C)C>[O:12]1[C:9]2=[CH:10][C:11]3[C:2]([NH:20][C:19]4[CH:21]=[CH:22][CH:23]=[C:17]([C:15]#[CH:16])[CH:18]=4)=[N:3][CH:4]=[N:5][C:6]=3[CH:7]=[C:8]2[O:14][CH2:13]1

Participants

4

Reactant 2

HCID 104682Benzenamine, 3-ethynyl-HCID 149353678-Chloro-2H-[1,3]dioxolo[4,5-g]quinazoline

Product 1

HCID 15549234N-(3-Ethynylphenyl)-2H-[1,3]dioxolo[4,5-g]quinazolin-8-amineYield 88.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 8-chloro-[1,3]dioxolo[4,5-g]quinazoline (0.200 g, 1.04 mmol) and 3-ethynylaniline (0.127 g, 1.09 mmol) in 5 mL isopropanol was heated to reflux overnight, then cooled to ambient temperature. Precipitate was collected and washed to give [1,3]dioxolo[4,5-g]quinazolin-8-yl-(3-ethynyl-phenyl)-amine (0.266 g, 78%): mp greater than 350° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customPrecipitate was collected
  4. washwashed

Sources & evidence

ORD record
ord-9ffb0180af664b7a9fc7bf646cd94d8f
Source dataset
uspto-grants-2002_01
Patent number
US06335344B1

Reaction notes

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