Ammonia → HCID 9925679, compound

HRID 374758Notes

Reaction equation

HRID 374758 reaction equation
[NH3:1].C(O[C:6]1[C:9](=[O:10])[C:8](=[O:11])[C:7]=1[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22]#[N:23])[CH:20]=2)[O:15][C:14]([CH3:25])([CH3:24])[CH:13]=1)(C)C>C(#N)C>[NH2:1][C:6]1[C:9](=[O:10])[C:8](=[O:11])[C:7]=1[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22]#[N:23])[CH:20]=2)[O:15][C:14]([CH3:24])([CH3:25])[CH:13]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 15291206HCID 15291206, compound

Product 1

HCID 9925679HCID 9925679, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ammonia gas was bubbled into a solution of 361 mg (1.12 mmol) of 4-(2-isopropoxy-3,4-dioxo-cyclobut-1-enyl)-2,2-dimethyl-2H-chromene-6-carbonitrile in acetonitrile (11 ml) for 30 min. The reaction mixture was stirred at ambient temperature for 16 h. The reaction mixture was quenched with H2O (50 mL) and was extracted into 20% THF-CH2Cl2. The combined organic extracts were dried over anhydrous Na2SO4 and then concentrated and recrystallized from acetone-petroleum ether to give 110 mg of the title compound (35% yield), mp>250° C., as an off white solid: 1H-NMR (DMSO-d6 ; 400 MHz) δ9.18 (bs, 1H), 8.68 (bs, 1H), 7.79 (d, 1H), 7.67 (dd, 1H), 7.01 (d, 1H), 6.29 (s, 1H), and 1.47 ppm (s, 6H); IR (KBr) 3300, 3100, 1780, 1730, 1720, 1665, and 1610 cm-1 ; mass spectrum (PBEI), m/e 281 (M+H), 280 (M+), 252, and 209.

Workup

  1. customThe reaction mixture was quenched with H2O (50 mL)
  2. extractionwas extracted into 20% THF-CH2Cl2
  3. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customrecrystallized from acetone-petroleum ether

Sources & evidence

ORD record
ord-c280ca3ff72c48a8b01419b682c25a10
Source dataset
uspto-grants-1996_01
Patent number
US05482942

Reaction notes

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