Stannous Chloride → N4-(3-ethynylphenyl)quinazoline-4,7-diamine

HRID 1968647Notes

Reaction equation

HRID 1968647 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([N+:20]([O-])=O)=[CH:17][CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2].Cl[Sn]Cl>C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([NH2:20])=[CH:17][CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 16045519N-(3-ethynylphenyl)-7-nitroquinazolin-4-amine

Product 1

HCID 16045588N4-(3-ethynylphenyl)quinazoline-4,7-diamineYield 89.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-(3-ethynylphenyl)-7-nitroquinazolin-4-amine (2.0 g, 6.89 mmol), SnCl2 (5.0 g, 26.37 mmol), and ethyl acetate (50 mL) was refluxed for 3 h. The mixture was subjected to extraction with ethyl acetate (20 mL). The combined organic layers were washed with brine (20 mL×2), dried over Na2SO4, and concentrated in vacuo to afford 1.6 g (86%) of N4-(3-ethynylphenyl)quinazoline-4,7-diamine as a yellow solid.

Workup

  1. extractionThe mixture was subjected to extraction with ethyl acetate (20 mL)
  2. washThe combined organic layers were washed with brine (20 mL×2)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b37fa2a9993f44b5a24f7ffb32c8bb5f
Source dataset
uspto-grants-2013_04
Patent number
US08426430B2

Reaction notes

Loading…