Water → 1000771-62-9

HRID 409561Notes

Reaction equation

HRID 409561 reaction equation
[OH:1][CH:2](CO)[CH2:3][N:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][CH2:6][C:5]1=[O:14].O>CO>[O:14]=[C:5]1[N:4]([CH2:3][CH:2]=[O:1])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][CH2:6]1

Participants

4

Reactant 2

HCID 962WaterHCID 59662175HCID 59662175, compound

Product 1

HCID 509908121000771-62-9Yield 84.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 1-3 (1.69 g, 7.58 mmol) was dissolved in MeOH (126 mL) and H2O (25 mL) in a 300 mL round bottom flask at rt, and treated with NalO4 (4.86 g, 23.0 mmol). After 2 hrs the solid was filtered, washing with methanol. The filtrate was concentrated to a white solid, taken up in dichloromethane (50 mL), washed with water (3×) and brine, then dried over sodium sulfate, and concentrated to give Compound 1-4 as a white solid (1.23 g, 83%, mp=97.1-98.0° C.). 1H NMR (500 MHz, CDCl3) δ 9.68 (s, 1H), 7.04-7.00 (m, 3H), 6.68-6.65 (m, 1H), 4.73 (s, 2H), 4.70 (s, 2H); 13C NMR (125 MHz, CDCl3) 195, 165.2, 145.3, 128.7, 124.7, 123.2, 117.6, 114.7, 67.6, 51.2; Anal Calcd. for C10H9NO3: C, 62.82; H, 4.74; N, 7.33. Found: C, 62.85; H, 4.46; N, 7.22.

Workup

  1. filtrationAfter 2 hrs the solid was filtered
  2. washwashing with methanol
  3. concentrationThe filtrate was concentrated to a white solid
  4. washwashed with water (3×) and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-471020abe0084b31b078c263ea4c87fe
Source dataset
uspto-grants-2014_06
Patent number
US08759342B2

Reaction notes

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