Acetic Acid → HCID 58514945, compound

HRID 1404804Notes

Reaction equation

HRID 1404804 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-a94f52530d26480db33af5af1bf60175
Source dataset
uspto-grants-2014_12
Patent number
US08912331B2

Reaction notes

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