Acetic Acid → HCID 58514945, compound

HRID 449297Notes

Reaction equation

HRID 449297 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[C:16]4=[N:17][C:18]([C:21]5[CH:22]=[N:23][N:24]([CH2:26][CH2:27][OH:28])[CH:25]=5)=[CH:19][CH:20]=[C:15]4[N:14]=[N:13]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(O)(=[O:31])C>OO>[OH:28][CH2:27][CH2:26][N:24]1[CH:25]=[C:21]([C:18]2[N:17]=[C:16]3[N:12]([CH2:11][C:7]4[CH:6]=[C:5]5[C:10](=[CH:9][CH:8]=4)[N+:1]([O-:31])=[CH:2][CH:3]=[CH:4]5)[N:13]=[N:14][C:15]3=[CH:20][CH:19]=2)[CH:22]=[N:23]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 53261809HCID 53261809, compound

Product 1

HCID 58514945HCID 58514945, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 784Hydrogen PeroxideSolvent

Procedure

To a solution of example 146 (0.100 g, 0.269 mmol) in acetic acid (1 ml), hydrogen peroxide solution (50%, 1 ml) and heated to 100° C. After 12 h, the mixture was concentrated, extracted with chloroform, washed with brine, dried over sodium sulphate and concentrated. The crude product was purified by column chromatography using dichloromethane: methanol to afford the title compound as an off-white solid (0.015 g, 14%). M.P.: 222-224° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 8.58-8.48 (m, 4H), 8.19 (s, 1H), 8.08 (s, 1H), 7.93 (d, J=8.5 Hz, 1H), 7.85 (dd, J=9.0, 1.8 Hz, 1H), 7.82 (d, J=8.8 Hz, 1H), 7.47 (dd, J=8.4, 6.0 Hz, 1H), 6.12 (s, 2H), 4.95 (t, J=5.2 Hz, 1H), 4.22 (t, J=5.5 Hz, 2H), 3.77 (q, J=5.5 Hz, 2H).

Workup

  1. concentrationthe mixture was concentrated
  2. extractionextracted with chloroform
  3. washwashed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-7815f8ba0618408291aec625b53cf1d4
Source dataset
uspto-grants-2013_07
Patent number
US08481739B2

Reaction notes

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