Water → HCID 10823521, compound

HRID 1455888Notes

Reaction equation

HRID 1455888 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][C:8]=2[CH:16]=1)([O-])=O.[C:17](OC(=O)C)(=[O:19])[CH3:18].CN(C1C=CC=CN=1)C.O>C(OCC)(=O)C.[Pd]>[NH:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][C:8]=2[CH:16]=1)[C:17]([CH3:18])=[O:19]

Participants

7

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 12148807Methyl 5-nitrobenzofuran-2-carboxylate

Product 1

HCID 10823521HCID 10823521, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 5-nitrobenzofuran-2-carboxylate (13, 0.5 g, 2.26 mmol, made from 5-nitrobenzofuran-2-carboxylic acid, Trans World Chemicals, Inc.) was dissolved in ethyl acetate (40 mL) and 5% Pd/C (30 mg) was added. The reaction mixture was hydrogenated for 1 h at room temperature at a pressure of 60 lb/inch2. The reaction mixture was filtered and the solvent was removed in vacuo. The residue was dissolved in acetone (10 mL) and was used without further purification. Acetic anhydride (0.86 mL, 9.1 mmol) and dimethylaminopyridine (20 mg) was added. The solution was stirred for 1 h at room temperature. Water (20 mL) was added and the mixture was extracted with ethyl acetate (40 mL×5). The solution was dried using sodium sulfate and solvent was removed in vacuo. A grey powder 9 was obtained (321 mg, 61% yield). An analytical sample was recrystallized in ethyl acetate. mp: 158°-159° C. 1H NMR (DMSO-d6, ppm): 10.03 (s, 1 H, NH), 8.19-8.18 (d, 1 H, J=1.6 Hz, Ar--H), 7.76-7.75 (d, 1 H, J=1.1 Hz, Ar--H), 7.65-7.63 (d, 1 H, J=9.0 Hz, Ar--H), 7.55-7.52 (dd, 2 H, J=2.3, 8.9 Hz, Ar--H), 3.89 (s, 1 H, OCH3), 2.07 (s, 3 H, CH3CO), Anal. (C12H11 NO4), C, H, N.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in acetone (10 mL)
  4. customwas used without further purification
  5. extractionthe mixture was extracted with ethyl acetate (40 mL×5)
  6. customThe solution was dried
  7. customwas removed in vacuo

Sources & evidence

ORD record
ord-8df9ab879e83423f9980d2078d5bff00
Source dataset
uspto-grants-1998_12
Patent number
US05843937

Reaction notes

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