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

HRID 1968635Notes

Reaction equation

HRID 1968635 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

A mixture of 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, and then subeject to extraction with ethyl acetate (20 mL) twice. The combined organic layers were washed with brine (20 mL) twice, 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. temperaturewas refluxed for 3 h
  2. extractionsubeject to extraction with ethyl acetate (20 mL) twice
  3. washThe combined organic layers were washed with brine (20 mL) twice
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-75e5544aff7944c19a83dc1633a1bd0e
Source dataset
uspto-grants-2013_04
Patent number
US08426430B2

Reaction notes

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