Acetic Anhydride → HCID 69004589, compound

HRID 1786526Notes

Reaction equation

HRID 1786526 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]2[O:10][CH2:11][O:12][C:5]2=[CH:4][C:3]=1[C:13]1[O:14][C:15]2[C:20]([CH2:21][CH:22]=1)=[CH:19][CH:18]=[C:17]([N:23]([CH3:25])[CH3:24])[CH:16]=2.[C:26](OC(=O)C)(=[O:28])[CH3:27]>N1C=CC=CC=1.CCCCCC.CCOC(C)=O>[C:26]([NH:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]2[O:10][CH2:11][O:12][C:5]2=[CH:4][C:3]=1[C:13]1[O:14][C:15]2[C:20]([CH2:21][CH:22]=1)=[CH:19][CH:18]=[C:17]([N:23]([CH3:25])[CH3:24])[CH:16]=2)(=[O:28])[CH3:27]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 69004803HCID 69004803, compound

Product 1

HCID 69004589HCID 69004589, compoundYield 8.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of 2-amino-3-cyano-7-dimethylamino-4-(methylenedioxy)phenyl-4H-chromene (43 mg, 0.13 mmol) in pyridine (1 ml) was added acetic anhydride (0.25 ml, 2.6 mmol) at room temperature. The mixture was stirred at room temperature for 3 days, then diluted with 1:1 hexane/EtOAc (40 ml), washed with water, 2N HCl, water, 2N NaOH, water and brine. The organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography (3:2 hexane/EtOAc) to yield the title compound as a yellow solid (4 mg, 8%). 1H NMR (CDCl3): 6.84-6.73 (m, 4H), 6.50-6.46 (m, 1H), 6.31 (m, 1H), 5.95, 5.94 (2s, 2H), 4.79 (s, 1H), 2.94 (s, 6H), 2.18 (s, 3H).

Workup

  1. washwashed with water, 2N HCl, water, 2N NaOH, water and brine
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography (3:2 hexane/EtOAc)

Sources & evidence

ORD record
ord-d27353f34a1b4168a72fadcaff16e6f7
Source dataset
uspto-grants-2009_03
Patent number
US07507762B2

Reaction notes

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