Tert-Butyl nitrite → HCID 10059873, compound

HRID 1453988Notes

Reaction equation

HRID 1453988 reaction equation
C(ON=O)(C)(C)C.[C:8]([C:10]1[CH:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:18]2[C:13](=[CH:14][C:15](N)=[CH:16][CH:17]=2)[O:12][C:11]=1N)#[N:9]>CN(C=O)C>[C:8]([C:10]1[CH:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[O:12][CH:11]=1)#[N:9]

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 28388372,7-Diamino-4-phenyl-4H-chromene-3-carbonitrile

Product 1

HCID 10059873HCID 10059873, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a three-neck RB flask equipped with a thermometer and a condenser containing anhydrous DMF (1 mL) at 65° C. was added tert-butylnitrite (0.4 mL, 3.02 mmol), followed by slow addition of 3-cyano-2,7-diamino-4-phenyl-4H-chromene (263 mg, 1.0 mmol) in anhydrous DMF (1 mL) in 10 min. The reaction was stirred further for 5 min, then quenched with addition of water (10 mL). The mixture was extracted with EtOAc (3×10 mL). The EtOAc was washed with water (5 mL), brine (5 mL), dried over MgSO4, and evaporated. The red residue was purified by chromatography on silica gel with EtOAc and hexane (1:4) as eluant to yield 64 mg (26%) of the product as an off-white solid. 1H NMR (CDCl3): 7.4-7.18 (m, 7H), 7.07-7.01 (m, 2H), 6.96-6.62 (m, 1H), 4.77 (s, 1H).

Workup

  1. customTo a three-neck RB flask equipped with a thermometer and a condenser
  2. customquenched with addition of water (10 mL)
  3. extractionThe mixture was extracted with EtOAc (3×10 mL)
  4. washThe EtOAc was washed with water (5 mL), brine (5 mL)
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe red residue was purified by chromatography on silica gel with EtOAc and hexane (1:4) as eluant

Sources & evidence

ORD record
ord-f379841d9fdd4f26b4fc38546c2cbe8b
Source dataset
uspto-grants-2009_01
Patent number
US07476741B2

Reaction notes

Loading…