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

HRID 1051233Notes

Reaction equation

HRID 1051233 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

To a solution of 4-chloro-7-fluoro-6-nitroquinazoline (12 g, 0.052 mol) in 120 mL DCM in an ice bath was added slowly a solution of 3-ethynylaniline (7 g, 0.060 mol) in 200 mL isopropanol. The reaction solution was stirred for 1 hour, then TEA (7 g, 0.069 mol) was added and stirred for another 0.5 hour at room temperature. The resulting solid precipitate was filtered and washed with 20 mL isopropanol twice, 20 mL H2O for twice, and dried to give N-(3-ethynylphenyl)-7-fluoro-6-nitroquinazolin-4-amine as yellow solid 8.2 g (50.3% yield).

Workup

  1. stirringstirred for another 0.5 hour at room temperature
  2. filtrationThe resulting solid precipitate was filtered
  3. washwashed with 20 mL isopropanol twice
  4. dry with material20 mL H2O for twice, and dried

Sources & evidence

ORD record
ord-263c52c7d7c04fe7ba0d379bedb81f1a
Source dataset
uspto-grants-2016_07
Patent number
US09388170B2

Reaction notes

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