3-Acetamido-6-nitrochromen-2-one → NSC359701

HRID 643223Notes

Reaction equation

HRID 643223 reaction equation
[BH4-].[Na+].[C:3]([NH:6][C:7]1[C:8](=[O:20])[O:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([N+:17]([O-])=O)=[CH:12][CH:11]=2)(=[O:5])[CH3:4]>O.CO.[Pd]>[C:3]([NH:6][C:7]1[C:8](=[O:20])[O:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([NH2:17])=[CH:12][CH:11]=2)(=[O:5])[CH3:4]

Participants

6

Reactant 2

HCID 7348923-Acetamido-6-nitrochromen-2-oneHCID 4311764Sodium borohydride

Product 1

HCID 338232NSC359701Yield 57%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Palladium 10 wt % on activated carbon (0.322 g, 1/10th the mass of 1) was placed in a 1-L round-bottom flask and the flask was purged with nitrogen. A solution of sodium borohydride (1.21 g, 32.9 mmol) in 22.6 mL water was added drop-wise. A suspension of compound 1 (3.20 g, 12.9 mmol) in methanol (775 mL) was then added over a two hour period and allowed to stir at room temperature an additional 30 min, when the reaction mixture was filtered through Celite and the solvent was removed by rotary evaporation. Water (750 mL) was added to the residue and the solution was cooled to 4° C. for 20 h. The resulting precipitate was filtered and rinsed with cold distilled water. The solid was recrystallized from ethanol to give 2 as a yellow solid (1.59 g, 7.3 mmol) in 57% yield. mp 250-252° C. (lit 252-253° C.). FTIR (KBr) (cm−1): 3410, 3310, 1700, 1650, 1630. 1H-NMR (DMSO-d6): δ (ppm) 9.65 (s, 1H), 8.40 (s, 1H), 7.10 (dd, J=9.1 Hz, J=2.7 Hz, 1H), 6.73 (d, J=9.1 Hz, 1H), 6.68 (d, J=2.7 Hz, 1H), 5.19 (bs, 2H), 2.14 (s, 3H). 13C-NMR (DMSO-d6): δ (ppm) 171.12, 158.78, 146.92, 142.52, 125.26, 124.98, 120.82, 117.54, 117.15, 110.66, 24.93. HRMS expected, 219.07770; found, 219.07697. Elemental analysis for C11H10N2O3: expected: C, 60.55; H, 4.62; N, 12.84; found: C, 60.15; H, 4.50; N, 12.62.

Workup

  1. customthe flask was purged with nitrogen
  2. additionwas then added over a two hour period
  3. filtrationwhen the reaction mixture was filtered through Celite
  4. customthe solvent was removed by rotary evaporation
  5. additionWater (750 mL) was added to the residue
  6. temperaturethe solution was cooled to 4° C. for 20 h
  7. filtrationThe resulting precipitate was filtered
  8. washrinsed
  9. distillationwith cold distilled water
  10. customThe solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-04118b5f200840808a81d2c31026ca74
Source dataset
uspto-grants-2010_04
Patent number
US07700375B2

Reaction notes

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