Potassium Carbonate → 5-Amino-2,2-dimethyl-2H-chromene-8-carbonitrile

HRID 501522Notes

Reaction equation

HRID 501522 reaction equation
[CH3:1][C:2]1([CH3:17])[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([C:15]#[N:16])[CH:6]=[CH:7][C:8]=2[N+:12]([O-])=O)[O:3]1.Cl[Sn]Cl.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O>[NH2:12][C:8]1[CH:7]=[CH:6][C:5]([C:15]#[N:16])=[C:4]2[C:9]=1[CH:10]=[CH:11][C:2]([CH3:17])([CH3:1])[O:3]2

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 24479Stannous ChlorideHCID 597542382,2-Dimethyl-5-nitro-2H-chromene-8-carbonitrile

Product 1

HCID 597542965-Amino-2,2-dimethyl-2H-chromene-8-carbonitrileYield 79.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of compound 6B (230 mg, 1 mmol) in EtOAc (5 mL) was added SnCl2 2H2O (780 mg, 3.5 mmol). The resulting mixture was stirred at rt for 20 h, then saturated aqueous K2CO3 was added. After stirring for 30 min, the reaction was treated with solid K2CO3 (550 mg). The resulting suspension was stirred at rt for another 2 h, and then filtered. The filtrate was concentrated under reduced pressure to give a crude product, which was chromatographed (silica gel) eluting with 20% to 60% EtOAc/hexane to afford the title compound (160 mg) as a light yellow oil.

Workup

  1. stirringAfter stirring for 30 min
  2. stirringThe resulting suspension was stirred at rt for another 2 h
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto give a crude product, which
  6. customwas chromatographed (silica gel)
  7. washeluting with 20% to 60% EtOAc/hexane

Sources & evidence

ORD record
ord-a811f8115fd2468fb9669bec4cbc23d1
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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