Benzenamine, 3-ethynyl- → N-(3-ethynylphenyl)-7-fluoro-6-nitroquinazolin-4-amine

HRID 1051118Notes

Reaction equation

HRID 1051118 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:15])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[C:16]([C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21])#[CH:17]>C(Cl)Cl.C(O)(C)C>[C:16]([C:18]1[CH:19]=[C:20]([NH:21][C:2]2[C:11]3[C:6](=[CH:7][C:8]([F:15])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][N:3]=2)[CH:22]=[CH:23][CH:24]=1)#[CH:17]

Participants

5

Reactant 2

HCID 104682Benzenamine, 3-ethynyl-HCID 106093584-Chloro-7-fluoro-6-nitroquinazoline

Product 1

HCID 59142759N-(3-ethynylphenyl)-7-fluoro-6-nitroquinazolin-4-amineYield 51.2%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

4-chloro-7-fluoro-6-nitroquinazoline (12 g, 0.052 mol) was dissolved in 120 ml DCM. A solution of 3-ethynylaniline (7 g, 0.057 mol) in 200 ml isopropanol was added dropwise in an ice bath. The solution was stirred for 1 hour in the ice bath, then TEA (7 g, 0.069 mol) was added and allowed to stir for another 0.5 hour at room temperature. Yellow precipitate was formed and the solid was filtered and washed with 20 ml isopropanol twice, dried to give N-(3-ethynylphenyl)-7-fluoro-6-nitroquinazolin-4-amine 8.2 g as a yellow solid (50.3% yield).

Workup

  1. customYellow precipitate was formed
  2. filtrationthe solid was filtered
  3. washwashed with 20 ml isopropanol twice
  4. customdried

Sources & evidence

ORD record
ord-cbb26f4631444c54b9b52cf3c9f30061
Source dataset
uspto-grants-2016_07
Patent number
US09388160B2

Reaction notes

Loading…