Tert-Butyl nitrite → HCID 14168963, compound

HRID 1826971Notes

Reaction equation

HRID 1826971 reaction equation
C(ON=O)(C)(C)C.[NH2:8][C:9]1[O:10][C:11]2[C:16]([CH:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:18]=1[C:19]#[N:20])=[CH:15][CH:14]=[C:13](N)[CH:12]=2>CN(C=O)C>[NH2:8][C:9]1[O:10][C:11]2[C:16]([CH:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:18]=1[C:19]#[N:20])=[CH:15][CH:14]=[CH:13][CH:12]=2

Participants

4

Reactant 2

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

Product 1

HCID 14168963HCID 14168963, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of t-butylnitrite (0.027 g, 0.26 mmol) in anhydrous DMF was added 2,7-diamino-3-cyano-4-phenyl-4H-chromene (53 mg, 0.201 mmol) in one portion. The reaction was immediately immersed into a 65° C. oil bath. Gas evolution occurred slowly. After stirring at 65° C. for 1.5 h, the reaction was quenched with addition of water (5 mL), and extracted with EtOAc (3×10 mL). The EtOAc extracts were washed with brine (2×5 mL), dried over MgSO4, and evaporated. The red residue was purified by chromatography on silica gel with EtOAc and hexane (1:2) as eluant to yield 6 mg (12%) of the title compound as a light yellow solid. 1H NMR (CD3Cl, 300 MHz): 7.35–7.17 (m, 6H), 7.06–6.96 (m, 3H), 4.75 (s, 1H), 4.61 (brs, 2H).

Workup

  1. customwas immediately immersed into a 65° C.
  2. customthe reaction was quenched with addition of water (5 mL)
  3. extractionextracted with EtOAc (3×10 mL)
  4. washThe EtOAc extracts were washed with brine (2×5 mL)
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe red residue was purified by chromatography on silica gel with EtOAc and hexane (1:2) as eluant

Sources & evidence

ORD record
ord-514730c07c9648799b2a2ef0f167463a
Source dataset
uspto-grants-2006_05
Patent number
US07053117B2

Reaction notes

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